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85329-86-8

Basic Information
CAS No.: 85329-86-8
Name: Desethylcarbamoyl Cabergoline
Article Data: 3
Molecular Structure:
Molecular Structure of 85329-86-8 (Desethylcarbamoyl Cabergoline)
Formula: C23H32N4O
Molecular Weight: 380.533
Synonyms: Cabergoline specified impurity D;Cabergoline related compound D;Desethylcarbamoyl Cabergoline;UNII-114UFJ65CL;
Density: 1.13g/cm3
Melting Point: 188-190°C
Boiling Point: 607.7°C at 760 mmHg
Flash Point: 321.3°C
PSA: 54.86000
LogP: 3.53020
Synthetic route
72821-79-5

methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

109-55-7

1-amino-3-(dimethylamino)propane

85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions
ConditionsYield
In acetic acid Heating;85%
With 2-hydroxypyridin In ethylene glycol at 100℃; for 18h;85%
With acetic acid for 24h; Reflux;74%
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dmap / dichloromethane / 16 h / Reflux; Inert atmosphere
2: zinc / methanol; acetic acid / 1.08 h / 20 °C
3: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
4: acetic acid / 24 h / Reflux
View Scheme
80993-64-2

9-methyl 7-(2,2,2-trichloroethyl) (6aR,9R,10aR)-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-7,9(4H)-dicarboxylate

85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: zinc / methanol; acetic acid / 1.08 h / 20 °C
2: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
3: acetic acid / 24 h / Reflux
View Scheme
30341-92-5

methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate

85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
2: acetic acid / 24 h / Reflux
View Scheme
25447-66-9

Dihydroergocryptine

85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: sodium hydroxide; sodium dithionite / water / 4 h / Reflux
2: sulfuric acid / 15 h / 20 °C
3: dmap / dichloromethane / 16 h / Reflux; Inert atmosphere
4: zinc / methanol; acetic acid / 1.08 h / 20 °C
5: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
6: acetic acid / 24 h / Reflux
View Scheme
5878-43-3

9,10-dihydrolysergic acid

85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sulfuric acid / 15 h / 20 °C
2: dmap / dichloromethane / 16 h / Reflux; Inert atmosphere
3: zinc / methanol; acetic acid / 1.08 h / 20 °C
4: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 35 °C
5: acetic acid / 24 h / Reflux
View Scheme
24424-99-5

di-tert-butyl dicarbonate

85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

474397-67-6

tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl]amino]carbonyl]ergoline-1-carboxylate

Conditions
ConditionsYield
With dmap In tetrahydrofuran at 40℃; for 2h;92%
18162-48-6

tert-butyldimethylsilyl chloride

85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

C29H46N4OSi

Conditions
ConditionsYield
Stage #1: (6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide With sodium hydride In tetrahydrofuran at 20℃; for 1.5h;
Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran at 20℃; for 1.25h;
86.5%
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

109-90-0

ethyl isocyanate

A

81409-90-7

cabergoline

B

126554-50-5

(6aR,9R,10aR)-7-allyl-N9-[3-(dimethylamino)propyl]-N4-ethyl-N9-(ethylcarbamoyl)-6a,7,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-4,9(6H)-dicarboxamide

Conditions
ConditionsYield
In toluene Heating;A 81%
B 0.57 g
85329-86-8

(6aR,9R,10aR)-7-allyl-N-[3-(dimethylamino)propyl]-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide

624-83-9

methyl isocyanate

126554-48-1

N-<3-(dimethylamino)propyl>-N-<(methylamino)-carbonyl>-6-(2-propenyl)-ergoline-8β-carboxamide

Conditions
ConditionsYield
80%
Downstream Products
81409-90-7
126554-49-2
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