2-Bromo-N-(5-chloro-2-pyridinyl)acetamide → 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[2-fluoro-4-(pyrrolidine-1-carbonyl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester

HRID 18609Notes

Reaction equation

HRID 18609 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14](=[O:30])[NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[O:23])=[CH:18][C:17]=3[F:29])[NH:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].Br[CH2:32][C:33]([NH:35][C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][N:37]=1)=[O:34]>>[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14](=[O:30])[NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([N:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)=[O:23])=[CH:18][C:17]=3[F:29])[N:10]([CH2:32][C:33](=[O:34])[NH:35][C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][N:37]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

3

Reactant 2

HCID 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamideHCID 686172772-[2-Fluoro-4-(pyrrolidine-1-carbonyl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester

Product 1

HCID 670133251-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[2-fluoro-4-(pyrrolidine-1-carbonyl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester

Procedure

1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[2-fluoro-4-(pyrrolidine-1-carbonyl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester was prepared by a procedure according to example 36 (ii) starting from 40.0 mg (0.10 mmol) 2-[2-Fluoro-4-(pyrrolidine-1-carbonyl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester and 29.2 mg (0.12 mmol) 2-bromo-N-(5-chloro-pyridin-2-yl)-acetamide. Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid) gave pure 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[2-fluoro-4-(pyrrolidine-1-carbonyl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester as a colorless amorphous solid.

Workup

  1. custom1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[2-fluoro-4-(pyrrolidine-1-carbonyl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester was prepared by a procedure
  2. customFinal purification by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid)

Sources & evidence

ORD record
ord-36cd88cb7e64490eba7c1101ca3525bf
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

Loading…