Boron tribromide → 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid

HRID 18543Notes

Reaction equation

HRID 18543 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[N:12]=[C:11]([C:14](=[O:29])[NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][C:23]4=[O:28])=[CH:18][CH:17]=3)[N:10]([CH2:30][C:31](=[O:40])[NH:32][C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][N:34]=3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].B(Br)(Br)Br>C(Cl)Cl>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([NH:32][C:31]([CH2:30][N:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[C:13]=3[N:12]=[C:11]2[C:14](=[O:29])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][C:23]3=[O:28])=[CH:18][CH:17]=2)=[O:40])=[N:34][CH:35]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 112038141-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester

Product 1

HCID 230334421-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

127 mg (0.20 mmol) 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid methyl ester were dissolved in 15 mL CH2Cl2. At 0° C. 1.8 mL (1.8 mmol) of a 1 M BBr3-solution were added. The reaction mixture was stirred for 24 h at room temperature. Because of incomplete conversion further 0.9 mL (0.9 mmol) of a 1 M BBr3-solution were added. After stirring for 24 h at room temperature the reaction mixture was concentrated and purified by preparative HPLC (CH3CN/H2O gradient+0.05% formic acid). 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-[4-(3-oxo-morpholin-4-yl)-phenylcarbamoyl]-1H-benzoimidazole-4-carboxylic acid was obtained as a light brown, amorphous solid. Yield: 73 mg MS (ES+): m/e=549, chloro pattern.

Workup

  1. customAt 0° C
  2. stirringAfter stirring for 24 h at room temperature the reaction mixture
  3. concentrationwas concentrated
  4. custompurified by preparative HPLC (CH3CN/H2O gradient+0.05% formic acid)

Sources & evidence

ORD record
ord-577eb697fd904a3a8070e36ebebb5489
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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