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

HRID 521799Notes

Reaction equation

HRID 521799 reaction equation
C[O:2][C:3](=[O:43])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([C:13]2[CH:17]=[C:16]([C:18]3[CH:23]=[C:22]([O:24][C:25]4[CH:30]=[CH:29][C:28]([NH:31][C:32]([NH:34][C:35]5[CH:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:36]=5[F:42])=[O:33])=[CH:27][CH:26]=4)[CH:21]=[CH:20][N:19]=3)[NH:15][CH:14]=2)=[O:12])[CH2:7][CH2:6]1.[OH-].[Na+].O.Cl>C1COCC1.CO>[F:42][C:36]1[CH:37]=[CH:38][C:39]([CH3:41])=[CH:40][C:35]=1[NH:34][C:32]([NH:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][C:22]2[CH:21]=[CH:20][N:19]=[C:18]([C:16]3[NH:15][CH:14]=[C:13]([C:11]([N:8]4[CH2:9][CH2:10][CH:5]([CH2:4][C:3]([OH:43])=[O:2])[CH2:6][CH2:7]4)=[O:12])[CH:17]=3)[CH:23]=2)=[CH:26][CH:27]=1)=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68403515methyl {1-[(5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]piperidin-4-yl}acetate

Product 1

HCID 69810773{1-[(5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]piperidin-4-yl}acetic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of methyl{1-[(5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]piperidin-4-yl}acetate (50 mg, 0.085 mmol) in THF/MeOH (5 ml/5 ml) was added 1M NaOH solution (3 ml, 3 mmol). The mixture was stirred at room temperature for one hour, and poured into 50 ml of water. 2M HCl was added until pH=4. The resulting precipitates were filtered, washed with water, and dried in vacuo to give {1-[(5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-1H-pyrrol-3-yl)carbonyl]piperidin-4-yl}acetic acid as white solid. Yield: 47 mg, 96%.

Workup

  1. customThe resulting precipitates
  2. filtrationwere filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-77ff454867f24b67aadd5fdd08c6cb7f
Source dataset
uspto-grants-2016_05
Patent number
US09328103B2

Reaction notes

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