((R)-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone

Base Information

• Chemical Name: ((R)-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone
• CAS No.: 1369958-94-0
• Molecular Formula: C₂₃H₂₃Cl₂N₅O₂
• Molecular Weight: 472.374
• Mol file: 1369958-94-0.mol

Synonyms:((R)-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone

Chemical Property of ((R)-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((R)-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone

There total 6 articles about ((R)-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone 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: 64.0%

C28H31Cl2N5O4 → ((R)-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone (1369958-94-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jm201386u

Reference yield:

methyl 7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate (1369959-19-2) → ((R)-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone (1369958-94-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

2.1: Chiral cell AD column / ethanol; n-heptane / Inert atmosphere; Resolution of racemate

3.1: lithium hydroxide / tetrahydrofuran; water / 15 h / 20 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 14 h / 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; lithium hydroxide; In tetrahydrofuran; ethanol; n-heptane; dichloromethane; water;

DOI:10.1021/jm201386u

Reference yield:

N-carbobenzyloxy-L-proline methyl ester (5211-23-4) → ((R)-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)((S)-2-(3-methylisoxazol-5-yl)pyrrolidin-1-yl)methanone (1369958-94-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / Inert atmosphere; Cooling

1.2: 1.5 h / Inert atmosphere; Heating

2.1: trifluorormethanesulfonic acid / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 14 h / 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

With n-butyllithium; trifluorormethanesulfonic acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jm201386u

upstream raw materials:

(R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylic acid

A 79814

methyl 7-(3,4-dichlorophenyl)-2,5-dimethyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-6-carboxylate

4-tert-butyl-6-methyl-7-(3,4-dichlorophenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine-4,6(7H)-dicarboxylate