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905854-02-6

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Basic Information
CAS No.: 905854-02-6
Name: 3-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione
Article Data: 4
Molecular Structure:
Molecular Structure of 905854-02-6 (3-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-pyrrolidine-2,5-dione)
Formula: C23H19 N3 O2
Molecular Weight: 369.423
Synonyms: (3R,4R)-3-(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione
Density: 1.49
Boiling Point: 715.95°C at 760 mmHg
Flash Point: 386.793°C
PSA: 66.89000
LogP: 3.92140
Related products
Synthetic route

(±)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione

A

905854-03-7

(+)-3(S),4(S)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-j]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione

B

905854-02-6

Tivantinib

Conditions
ConditionsYield
Purification / work up; Resolution of racemate;
With Chiralpak AZ column In methanol; dichloromethane; acetonitrile Resolution of racemate; Multicolumn chromatography;A n/a
B n/a
With CHIRALPAK AD column In methanol; carbon dioxide liquid CO2;
5840-01-7

5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline

905854-02-6

Tivantinib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: tert-butyl methyl ether / 2.17 h / 15 - 32 °C / Industry scale
1.2: 2 h / Industry scale
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 - 32 °C / Industry scale
2.2: 0.5 h / 40 - 50 °C / Industry scale
2.3: 40 °C / pH 8 - 9 / Industry scale
3.1: hydrogen; potassium tert-butylate / 20 % Pd(OH)2/C / tetrahydrofuran / 45 - 55 °C / 3361.55 - 4137.29 Torr / Industry scale
4.1: hydrogenchloride / water; Isopropyl acetate / Industry scale
5.1: Chiralpak AZ column / dichloromethane; acetonitrile; methanol / Resolution of racemate; Multicolumn chromatography
View Scheme
Multi-step reaction with 6 steps
1.1: tert-butyl methyl ether / 2.17 h / 15 - 32 °C / Industry scale
1.2: 2 h / Industry scale
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 - 32 °C / Industry scale
2.2: 0.5 h / 40 - 50 °C / Industry scale
2.3: 40 °C / pH 8 - 9 / Industry scale
3.1: hydrogen; potassium tert-butylate / 20 % Pd(OH)2/C / tetrahydrofuran / 45 - 55 °C / 3361.55 - 4137.29 Torr / Industry scale
4.1: hydrogenchloride / water; Isopropyl acetate / Industry scale
5.1: acetonitrile / 50 °C
6.1: hydrogenchloride / 3-methyltetrahydrofuran; water / 50 °C / pH 1.6
View Scheme
Multi-step reaction with 5 steps
1.1: tert-butyl methyl ether / 0.1 h / 20 - 32 °C / Inert atmosphere
1.2: 0.1 h / 25 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 20 - 32 °C / Inert atmosphere
2.2: 0.1 h / 0.4 - 0.5 °C
2.3: 0.01 h / 20 - 32 °C
3.1: potassium tert-butylate; 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran / 12 h / 0.45 - 0.5 °C / 3360.34 Torr
4.1: water; methanol / 3 h / 0.55 - 20 °C / Inert atmosphere
5.1: hydrogenchloride / methanol / 0.45 - 0.55 °C
View Scheme
345264-02-0

(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester

905854-02-6

Tivantinib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 - 32 °C / Industry scale
1.2: 0.5 h / 40 - 50 °C / Industry scale
1.3: 40 °C / pH 8 - 9 / Industry scale
2.1: hydrogen; potassium tert-butylate / 20 % Pd(OH)2/C / tetrahydrofuran / 45 - 55 °C / 3361.55 - 4137.29 Torr / Industry scale
3.1: hydrogenchloride / water; Isopropyl acetate / Industry scale
4.1: Chiralpak AZ column / dichloromethane; acetonitrile; methanol / Resolution of racemate; Multicolumn chromatography
View Scheme
Multi-step reaction with 5 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 - 32 °C / Industry scale
1.2: 0.5 h / 40 - 50 °C / Industry scale
1.3: 40 °C / pH 8 - 9 / Industry scale
2.1: hydrogen; potassium tert-butylate / 20 % Pd(OH)2/C / tetrahydrofuran / 45 - 55 °C / 3361.55 - 4137.29 Torr / Industry scale
3.1: hydrogenchloride / water; Isopropyl acetate / Industry scale
4.1: acetonitrile / 50 °C
5.1: hydrogenchloride / 3-methyltetrahydrofuran; water / 50 °C / pH 1.6
View Scheme
Multi-step reaction with 4 steps
1.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 20 - 32 °C / Inert atmosphere
1.2: 0.1 h / 0.4 - 0.5 °C
1.3: 0.01 h / 20 - 32 °C
2.1: potassium tert-butylate; 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran / 12 h / 0.45 - 0.5 °C / 3360.34 Torr
3.1: water; methanol / 3 h / 0.55 - 20 °C / Inert atmosphere
4.1: hydrogenchloride / methanol / 0.45 - 0.55 °C
View Scheme
345261-20-3

3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dion

905854-02-6

Tivantinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen; potassium tert-butylate / 20 % Pd(OH)2/C / tetrahydrofuran / 45 - 55 °C / 3361.55 - 4137.29 Torr / Industry scale
2: hydrogenchloride / water; Isopropyl acetate / Industry scale
3: Chiralpak AZ column / dichloromethane; acetonitrile; methanol / Resolution of racemate; Multicolumn chromatography
View Scheme
Multi-step reaction with 4 steps
1: hydrogen; potassium tert-butylate / 20 % Pd(OH)2/C / tetrahydrofuran / 45 - 55 °C / 3361.55 - 4137.29 Torr / Industry scale
2: hydrogenchloride / water; Isopropyl acetate / Industry scale
3: acetonitrile / 50 °C
4: hydrogenchloride / 3-methyltetrahydrofuran; water / 50 °C / pH 1.6
View Scheme
Multi-step reaction with 3 steps
1: potassium tert-butylate; 10 wt% Pd(OH)2 on carbon; hydrogen / tetrahydrofuran / 12 h / 0.45 - 0.5 °C / 3360.34 Torr
2: water; methanol / 3 h / 0.55 - 20 °C / Inert atmosphere
3: hydrogenchloride / methanol / 0.45 - 0.55 °C
View Scheme
905854-03-7

(+)-3(S),4(S)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-j]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione

905854-02-6

Tivantinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / ethanol / 13 h / 65 °C / Industry scale
1.2: 60 °C
2.1: acetonitrile / 50 °C
3.1: hydrogenchloride / 3-methyltetrahydrofuran; water / 50 °C / pH 1.6
View Scheme

(±)-cis-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione

905854-02-6

Tivantinib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; Isopropyl acetate / Industry scale
2: Chiralpak AZ column / dichloromethane; acetonitrile; methanol / Resolution of racemate; Multicolumn chromatography
View Scheme
Multi-step reaction with 3 steps
1: hydrogenchloride / water; Isopropyl acetate / Industry scale
2: acetonitrile / 50 °C
3: hydrogenchloride / 3-methyltetrahydrofuran; water / 50 °C / pH 1.6
View Scheme
1313508-66-5

(3R,4R)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione pseudoephedrine complex

905854-02-6

Tivantinib

Conditions
ConditionsYield
With hydrogenchloride In 3-methyltetrahydrofuran; water at 50℃; pH=1.6; Product distribution / selectivity;
With hydrogenchloride In methanol at 0.45 - 0.55℃;
635-46-1

1,2,3,4-tetrahydroisoquinoline

A

905854-03-7

(+)-3(S),4(S)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-j]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione

B

905854-02-6

Tivantinib

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: tetrahydrofuran / 24.5 h / 20 °C
2.1: magnesium chloride / 2-methoxy-ethanol / 6 h / 125 °C / Reflux
3.1: sodium hydroxide; water / ethanol / 2 h / Reflux
4.1: copper chromite / quinoline / 2 h / 185 °C
5.1: diethyl ether / 0 °C
5.2: -78 - 20 °C
6.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 °C
7.1: magnesium; methanol / 0.67 h / Inert atmosphere; Reflux
8.1: CHIRALPAK® AD column / methanol; carbon dioxide / liquid CO2
View Scheme
Multi-step reaction with 8 steps
1.1: tetrahydrofuran / 24.5 h / 20 °C
2.1: magnesium chloride / 2-methoxy-ethanol / 6 h / 125 °C / Reflux
3.1: sodium hydroxide; water / ethanol / 2 h / Reflux
4.1: copper chromite / quinoline / 2 h / 185 °C
5.1: diethyl ether / 0 °C
5.2: -78 - 20 °C
6.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 °C
7.1: zinc; mercury dichloride; hydrogenchloride / ethanol / Reflux
8.1: CHIRALPAK® AD column / methanol; carbon dioxide / liquid CO2
View Scheme
Multi-step reaction with 9 steps
1.1: tetrahydrofuran / 24.5 h / 20 °C
2.1: magnesium chloride / 2-methoxy-ethanol / 6 h / 125 °C / Reflux
3.1: sodium hydroxide; water / ethanol / 2 h / Reflux
4.1: copper chromite / quinoline / 2 h / 185 °C
5.1: diethyl ether / 0 °C
5.2: -78 - 20 °C
6.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 °C
7.1: palladium 10% on activated carbon; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
8.1: potassium tert-butylate / tert-butyl alcohol / 16 h / 50 °C
9.1: CHIRALPAK® AD column / methanol; carbon dioxide / liquid CO2
View Scheme
Multi-step reaction with 9 steps
1.1: tetrahydrofuran / 24.5 h / 20 °C
2.1: magnesium chloride / 2-methoxy-ethanol / 6 h / 125 °C / Reflux
3.1: sodium hydroxide; water / ethanol / 2 h / Reflux
4.1: copper chromite / quinoline / 2 h / 185 °C
5.1: diethyl ether / 0 °C
5.2: -78 - 20 °C
6.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 °C
7.1: zinc; mercury dichloride; hydrogenchloride / ethanol / Reflux
8.1: potassium tert-butylate / tert-butyl alcohol / 16 h / 50 °C
9.1: CHIRALPAK® AD column / methanol; carbon dioxide / liquid CO2
View Scheme
152712-44-2

3-(3,4-dihydro-2H-quinolin-1-yl)-2-oxopropionic acid ethyl ester

A

905854-03-7

(+)-3(S),4(S)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-j]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione

B

905854-02-6

Tivantinib

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: magnesium chloride / 2-methoxy-ethanol / 6 h / 125 °C / Reflux
2.1: sodium hydroxide; water / ethanol / 2 h / Reflux
3.1: copper chromite / quinoline / 2 h / 185 °C
4.1: diethyl ether / 0 °C
4.2: -78 - 20 °C
5.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 °C
6.1: zinc; mercury dichloride; hydrogenchloride / ethanol / Reflux
7.1: CHIRALPAK® AD column / methanol; carbon dioxide / liquid CO2
View Scheme
Multi-step reaction with 7 steps
1.1: magnesium chloride / 2-methoxy-ethanol / 6 h / 125 °C / Reflux
2.1: sodium hydroxide; water / ethanol / 2 h / Reflux
3.1: copper chromite / quinoline / 2 h / 185 °C
4.1: diethyl ether / 0 °C
4.2: -78 - 20 °C
5.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 °C
6.1: magnesium; methanol / 0.67 h / Inert atmosphere; Reflux
7.1: CHIRALPAK® AD column / methanol; carbon dioxide / liquid CO2
View Scheme
Multi-step reaction with 8 steps
1.1: magnesium chloride / 2-methoxy-ethanol / 6 h / 125 °C / Reflux
2.1: sodium hydroxide; water / ethanol / 2 h / Reflux
3.1: copper chromite / quinoline / 2 h / 185 °C
4.1: diethyl ether / 0 °C
4.2: -78 - 20 °C
5.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 °C
6.1: palladium 10% on activated carbon; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
7.1: potassium tert-butylate / tert-butyl alcohol / 16 h / 50 °C
8.1: CHIRALPAK® AD column / methanol; carbon dioxide / liquid CO2
View Scheme
Multi-step reaction with 8 steps
1.1: magnesium chloride / 2-methoxy-ethanol / 6 h / 125 °C / Reflux
2.1: sodium hydroxide; water / ethanol / 2 h / Reflux
3.1: copper chromite / quinoline / 2 h / 185 °C
4.1: diethyl ether / 0 °C
4.2: -78 - 20 °C
5.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 °C
6.1: zinc; mercury dichloride; hydrogenchloride / ethanol / Reflux
7.1: potassium tert-butylate / tert-butyl alcohol / 16 h / 50 °C
8.1: CHIRALPAK® AD column / methanol; carbon dioxide / liquid CO2
View Scheme
124730-53-6

5,6-dihydro-4H-pyrrolo [3,2,1-ij]quinoline-1-carboxylic acid ethyl ester

A

905854-03-7

(+)-3(S),4(S)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-j]quinolin-1-yl)-4-(1H-indol-3-yl)pyrrolidine-2,5-dione

B

905854-02-6

Tivantinib

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydroxide; water / ethanol / 2 h / Reflux
2.1: copper chromite / quinoline / 2 h / 185 °C
3.1: diethyl ether / 0 °C
3.2: -78 - 20 °C
4.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 °C
5.1: zinc; mercury dichloride; hydrogenchloride / ethanol / Reflux
6.1: CHIRALPAK® AD column / methanol; carbon dioxide / liquid CO2
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydroxide; water / ethanol / 2 h / Reflux
2.1: copper chromite / quinoline / 2 h / 185 °C
3.1: diethyl ether / 0 °C
3.2: -78 - 20 °C
4.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 °C
5.1: magnesium; methanol / 0.67 h / Inert atmosphere; Reflux
6.1: CHIRALPAK® AD column / methanol; carbon dioxide / liquid CO2
View Scheme
Multi-step reaction with 7 steps
1.1: sodium hydroxide; water / ethanol / 2 h / Reflux
2.1: copper chromite / quinoline / 2 h / 185 °C
3.1: diethyl ether / 0 °C
3.2: -78 - 20 °C
4.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 °C
5.1: palladium 10% on activated carbon; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr
6.1: potassium tert-butylate / tert-butyl alcohol / 16 h / 50 °C
7.1: CHIRALPAK® AD column / methanol; carbon dioxide / liquid CO2
View Scheme
Multi-step reaction with 7 steps
1.1: sodium hydroxide; water / ethanol / 2 h / Reflux
2.1: copper chromite / quinoline / 2 h / 185 °C
3.1: diethyl ether / 0 °C
3.2: -78 - 20 °C
4.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 °C
5.1: zinc; mercury dichloride; hydrogenchloride / ethanol / Reflux
6.1: potassium tert-butylate / tert-butyl alcohol / 16 h / 50 °C
7.1: CHIRALPAK® AD column / methanol; carbon dioxide / liquid CO2
View Scheme
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    China (Mainland)  |  Contact Details

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     China (Mainland)  |  Contact Details

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