Hydrochloric Acid → [({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]acetic acid

HRID 1402478Notes

Reaction equation

HRID 1402478 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:25]([C:28]([NH:30][C:31]2[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][C:32]=2[F:38])=[O:29])=[CH:24][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[NH:15][CH:14]=[C:13]([C:16]([NH:18][CH2:19][C:20]([O:22]C)=[O:21])=[O:17])[CH:12]=2)[CH:6]=1.C1COCC1.CO.[OH-].[Na+].Cl>O>[F:1][C:2]1[CH:27]=[CH:26][C:25]([C:28]([NH:30][C:31]2[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][C:32]=2[F:38])=[O:29])=[CH:24][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[NH:15][CH:14]=[C:13]([C:16]([NH:18][CH2:19][C:20]([OH:22])=[O:21])=[O:17])[CH:12]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 51001378methyl [({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]acetate

Product 1

HCID 51001377[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of methyl [({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]acetate (110 mg, 0.2 mmol) in a mixture of solvents THF/MeOH (5 ml/5 ml) was added 1M NaOH solution (1 ml, 1 mmol). The mixture was stirred at room temperature for 1 hour, and poured into 100 ml of water. 2M HCl was added until pH=4. The precipitates were filtered, washed with water and dried in vacuo to give [({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]acetic acid as white solid. Yield: 100 mg, 93%.

Workup

  1. filtrationThe precipitates were filtered
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-034c665b1e8b41c39756905fc2138292
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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