2-({(3aR,4S,6R,6aS)-6-[7-{[[N-(IR,2S)-2-(3,4-difluorophenyl)-cyclopropan-1-yl]-N-benzyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}oxy)ethanol

Base Information

• Chemical Name: 2-({(3aR,4S,6R,6aS)-6-[7-{[[N-(IR,2S)-2-(3,4-difluorophenyl)-cyclopropan-1-yl]-N-benzyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}oxy)ethanol
• CAS No.: 1383715-62-5
• Molecular Formula: C₃₃H₃₈F₂N₆O₄S
• Molecular Weight: 652.765
• Mol file: 1383715-62-5.mol

Synonyms:2-({(3aR,4S,6R,6aS)-6-[7-{[[N-(IR,2S)-2-(3,4-difluorophenyl)-cyclopropan-1-yl]-N-benzyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}oxy)ethanol

Chemical Property of 2-({(3aR,4S,6R,6aS)-6-[7-{[[N-(IR,2S)-2-(3,4-difluorophenyl)-cyclopropan-1-yl]-N-benzyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}oxy)ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-({(3aR,4S,6R,6aS)-6-[7-{[[N-(IR,2S)-2-(3,4-difluorophenyl)-cyclopropan-1-yl]-N-benzyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}oxy)ethanol

There total 15 articles about 2-({(3aR,4S,6R,6aS)-6-[7-{[[N-(IR,2S)-2-(3,4-difluorophenyl)-cyclopropan-1-yl]-N-benzyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}oxy)ethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

[3aR-[3aα,4α,6α,(1R,2S),6aα]]-2-[6-[[[7-(2-(3,4-difluorophenyl)cyclopropyl)]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenteno-1,3-dioxolan-4-yl]oxy]ethanol (274693-26-4) + benzyl bromide (100-39-0) → 2-({(3aR,4S,6R,6aS)-6-[7-{[[N-(IR,2S)-2-(3,4-difluorophenyl)-cyclopropan-1-yl]-N-benzyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}oxy)ethanol (1383715-62-5)

Guidance literature:

With potassium carbonate; In acetone; at 55 - 60 ℃; for 20h;

Reference yield:

tert-butyl [[(3aR,4S,6R,6aS)-6-(N,N-dibenzylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy]acetate (1383715-56-7) → 2-({(3aR,4S,6R,6aS)-6-[7-{[[N-(IR,2S)-2-(3,4-difluorophenyl)-cyclopropan-1-yl]-N-benzyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}oxy)ethanol (1383715-62-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: diisobutylaluminium hydride / toluene / 2.5 h / -25 - -20 °C

1.2: 0.25 h

2.1: hydrogen / 20% palladium hydroxide-activated charcoal / methanol / 10 h / 20 - 25 °C / 2327.23 Torr / Autoclave; Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C

4.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C

5.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C

6.1: iodine / acetone / 2 h / 25 - 60 °C

7.1: potassium carbonate / acetone / 20 h / 55 - 60 °C

With sodium azide; sodium dithionite; hydrogen; iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; 20% palladium hydroxide-activated charcoal; In tetrahydrofuran; methanol; water; acetone; toluene;

Reference yield:

(3aR,4S,6R,6aS)-6-(N,N-dibenzylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (1383715-55-6) → 2-({(3aR,4S,6R,6aS)-6-[7-{[[N-(IR,2S)-2-(3,4-difluorophenyl)-cyclopropan-1-yl]-N-benzyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}oxy)ethanol (1383715-62-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium t-butanolate / N,N-dimethyl-formamide; tetrahydrofuran / 2 h / -10 - 5 °C

2.1: diisobutylaluminium hydride / toluene / 2.5 h / -25 - -20 °C

2.2: 0.25 h

3.1: hydrogen / 20% palladium hydroxide-activated charcoal / methanol / 10 h / 20 - 25 °C / 2327.23 Torr / Autoclave; Inert atmosphere

4.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 20 - 25 °C

5.1: sodium hydrogencarbonate; sodium dithionite / water; acetone / 2 h / 20 - 25 °C

6.1: sodium azide; acetic acid / toluene; water / 1 h / 5 - 10 °C

7.1: iodine / acetone / 2 h / 25 - 60 °C

8.1: potassium carbonate / acetone / 20 h / 55 - 60 °C

With sodium azide; sodium dithionite; hydrogen; iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium t-butanolate; 20% palladium hydroxide-activated charcoal; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetone; toluene;

upstream raw materials:

[3aR-[3aα,4α,6α,(1R,2S),6aα]]-2-[6-[[[7-(2-(3,4-difluorophenyl)cyclopropyl)]amino-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenteno-1,3-dioxolan-4-yl]oxy]ethanol

benzyl bromide

4,6-dihydroxy-2-(propylsulfanyl)pyrimidine

4,6-dihydroxy-5-nitro-2-(propylthio)pyrimidine

Downstream raw materials:

ticagrelor

C₃₀H₃₄F₂N₆O₄S

Refernces