4-amino-N-[(1S)-1-(4-chlorophenyl)-3-pyrrolidin-1-ylpropyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

Base Information

• Chemical Name: 4-amino-N-[(1S)-1-(4-chlorophenyl)-3-pyrrolidin-1-ylpropyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide
• CAS No.: 1143533-32-7
• Molecular Formula: C₂₅H₃₂ClN₇O
• Molecular Weight: 482.028
• Mol file: 1143533-32-7.mol

Synonyms:

Chemical Property of 4-amino-N-[(1S)-1-(4-chlorophenyl)-3-pyrrolidin-1-ylpropyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-amino-N-[(1S)-1-(4-chlorophenyl)-3-pyrrolidin-1-ylpropyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

There total 8 articles about 4-amino-N-[(1S)-1-(4-chlorophenyl)-3-pyrrolidin-1-ylpropyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide 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: 10.0%

4-(tert-butoxycarbonylamino)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid (956460-96-1) + (S)-1-(4-chlorophenyl)-3-(pyrrolidin-1-yl)propan-1-amine (1296863-10-9) → 4-amino-N-[(1S)-1-(4-chlorophenyl)-3-pyrrolidin-1-ylpropyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (1143533-32-7)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,2-dimethoxyethane; for 16h; Inert atmosphere;

DOI:10.1021/jm301762v

Reference yield:

(S)-3-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propyl methanesulfonate (1143534-74-0) → 4-amino-N-[(1S)-1-(4-chlorophenyl)-3-pyrrolidin-1-ylpropyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (1143533-32-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 0.5 h / 120 °C / Microwave irradiation

1.2: 1 h / 20 °C

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / 1,2-dimethoxyethane / 16 h / Inert atmosphere

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; 1,2-dimethoxyethane;

DOI:10.1021/jm301762v

Reference yield:

(3S)-3-amino-3-(4-chlorophenyl)propan-1-ol (1213362-28-7,886061-26-3) → 4-amino-N-[(1S)-1-(4-chlorophenyl)-3-pyrrolidin-1-ylpropyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (1143533-32-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dichloromethane / 24 h / 20 - 25 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 0.75 h / 20 - 25 °C / Inert atmosphere

3.1: tetrahydrofuran / 0.5 h / 120 °C / Microwave irradiation

3.2: 1 h / 20 °C

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / 1,2-dimethoxyethane / 16 h / Inert atmosphere

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/jm301762v

upstream raw materials:

(3S)-3-amino-3-(4-chlorophenyl)propan-1-ol

tert-butyl (S)-(1-(4-chlorophenyl)-3-hydroxypropyl)carbamate

(S)-3-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propyl methanesulfonate

4-(tert-butoxycarbonylamino)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid