Hydrochloric Acid → 2-{2,6-Dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

HRID 1189654Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:32]([N:33]2[CH2:38][CH2:37][CH:36]([C:39]([F:42])([F:41])[F:40])[CH2:35][CH2:34]2)=[CH:31][C:9]2[N:10]([CH3:30])[C:11]([NH:13][C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([CH2:21][NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:15]=3[Cl:29])=[N:12][C:8]=2[CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[Cl:29][C:15]1[C:16]([CH2:21][NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[NH:13][C:11]1[N:10]([CH3:30])[C:9]2[CH:31]=[C:32]([N:33]3[CH2:34][CH2:35][CH:36]([C:39]([F:42])([F:41])[F:40])[CH2:37][CH2:38]3)[C:6]([C:4]([OH:5])=[O:3])=[CH:7][C:8]=2[N:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid ethyl ester (550 mg, 0.86 mmol), 1 N NaOH-solution (10 ml) and dioxane (20 ml) is stirred for 24 h at 100° C. and acidified with 1 N HCl (to pH ˜5). The mixture is extracted with EtOAc and the organic layer is washed with brine, dried with Na2SO4, filtered and concentrated.

Workup

extractionThe mixture is extracted with EtOAc
washthe organic layer is washed with brine
dry with materialdried with Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-b63d96f5f1db4cd9a7abff6f57dca4f3
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674113B2

Reaction notes

Loading…