Hydrochloric Acid → 5-{4-[3-(2-Fluoro-5-methyl-phenylcarbamoyl)-phenoxy]-pyridin-2-yl}-1H-pyrrole-3-carboxylic acid

HRID 521775Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23](=[O:33])[NH:24][C:25]4[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:26]=4[F:32])[CH:18]=3)[CH:13]=[CH:12][N:11]=2)[NH:7][CH:6]=1)=[O:4].[OH-].[Na+].O.Cl>C1COCC1>[F:32][C:26]1[CH:27]=[CH:28][C:29]([CH3:31])=[CH:30][C:25]=1[NH:24][C:23]([C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([C:8]2[NH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:9]=2)[CH:15]=1)=[O:33]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 5-{4-[3-(2-Fluoro-5-methyl-phenylcarbamoyl)-phenoxy]-pyridin-2-yl}-1H-pyrrole-3-carboxylic acid methyl ester (140 mg, 0.31 mmol) in THF (8 ml) was added 5M NaOH solution (1 ml, 5 mmol). The mixture was heated at 70° C. for 3 hours, cooled to room temp, and poured into 100 ml of water. 2M HCl was added until pH=4. The precipitates were filtered, washed with water, and dried to give 5-{4-[3-(2-Fluoro-5-methyl-phenylcarbamoyl)-phenoxy]-pyridin-2-yl}-1H-pyrrole-3-carboxylic acid as white solid.

Workup

temperaturecooled to room temp
filtrationThe precipitates were filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-1b23efd4ac6a433db4750ff0ad494059
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328103B2

Reaction notes

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