Sodium Hydroxide → 2-{2,6-Dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[3,3-difluoro-pyrrolidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

HRID 1189648Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:31]([N:32]2[CH2:36][CH2:35][C:34]([F:38])([F:37])[CH2:33]2)=[CH:30][C:8]2[N:9]([CH3:29])[C:10]([NH:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([CH2:20][NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[C:14]=3[Cl:28])=[N:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>CCO>[Cl:28][C:14]1[C:15]([CH2:20][NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=1[NH:12][C:10]1[N:9]([CH3:29])[C:8]2[CH:30]=[C:31]([N:32]3[CH2:36][CH2:35][C:34]([F:37])([F:38])[CH2:33]3)[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[N:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[3,3-difluoro-pyrrolidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid methyl ester (2.37 g, 4.17 mmol), 2 N NaOH-solution (9.8 ml) and EtOH (20 ml) is stirred for 1 h at rt and for 2 h at 50° C. and concentrated. Water is added and it is filtered. The filtrate is acidified with 4N HCl (pH 5) and the precipitate is filtered, washed with water and dried.

Workup

concentrationconcentrated
additionWater is added
filtrationit is filtered
filtrationthe precipitate is filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-bb81945c7e944761818072c6d1ca62a8
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674113B2

Reaction notes

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