Hydrochloric Acid → 7-[4-({[(2-Fluoro-5-methylphenyl)amino]carbonyl}amino)phenyl]thieno[3,2-b]pyridine-2-carboxylic acid

HRID 2407211Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]3[CH:25]=[C:26]([C:28]([O:30]C)=[O:29])[S:27][C:20]=23)=[CH:15][CH:14]=1)=[O:11].[OH-].[Na+].O.Cl>C1COCC1.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]3[CH:25]=[C:26]([C:28]([OH:30])=[O:29])[S:27][C:20]=23)=[CH:17][CH:18]=1)=[O:11]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of methyl 7-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenyl]thieno[3,2-b]pyridine-2-carboxylate (20 mg, 0.046 mmol) in THF/MeOH (5 ml/5 ml) was added 1M NaOH (2.0 ml, 2.0 mmol). The mixture was heated at 70° C. for 30 minutes, cooled to room temperature and poured into 50 ml of water. 1M HCl was added until pH=4 and the resulting precipitates were filtered, washed with water and dried in vacuo to give 7-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenyl]thieno[3,2-b]pyridine-2-carboxylic acid.

Workup

temperaturecooled to room temperature
customthe resulting precipitates
filtrationwere filtered
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-a663f256ed42491599f983b6e3f1c1b8
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809534B2

Reaction notes

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