Hydrochloric Acid → 5-[4-({3-[(3-methyl-2-furoyl)amino]phenyl}amino)pyridin-2-yl]-1H-pyrrole-3-carboxylic acid

HRID 521768Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of methyl 5-[4-({3-[(3-methyl-2-furoyl)amino]phenyl}amino)pyridin-2-yl]-1H-pyrrole-3-carboxylate (10 mg, 0.024 mmol) in a mixture of solvents THF/MeOH (5 ml/5 ml) was added 2 ml of 1M NaOH (2 mmol) solution. The mixture was heated in a 60° C. bath for 16 hours, cooled to room temperature and poured into 100 ml of water. 2M HCl was added until pH=5. The resulting precipitates were filtered, washed with water, and dried in vacuo to give 5-[4-({3-[(3-methyl-2-furoyl)amino]phenyl}amino)pyridin-2-yl]-1H-pyrrole-3-carboxylic acid as light brown solid. Yield: 2 mg.

Workup

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

Sources & evidence

ORD record: ord-6d3fb279993d4f0f8fa3cb36a07bede3
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328103B2

Reaction notes

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