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

HRID 1402589Notes

Reaction equation

HRID 1402589 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:31]([C:34]([NH:36][C:37]2[CH:42]=[C:41]([CH3:43])[CH:40]=[CH:39][C:38]=2[F:44])=[O:35])=[CH:30][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][CH:19]([CH2:24][CH2:25][C:26]([O:28]C)=[O:27])[C:20]([O:22]C)=[O:21])=[O:17])[CH:12]=2)[CH:6]=1.[OH-].[Na+].O.Cl>CO>[F:1][C:2]1[CH:33]=[CH:32][C:31]([C:34]([NH:36][C:37]2[CH:42]=[C:41]([CH3:43])[CH:40]=[CH:39][C:38]=2[F:44])=[O:35])=[CH:30][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][CH:19]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:20]([OH:22])=[O:21])=[O:17])[CH:12]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 71293583dimethyl 2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanedioate

Product 1

HCID 712935772-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanedioic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of dimethyl 2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanedioate (320 mg, 0.53 mmol) in MeOH (20 ml) was added 1M NaOH solution (2 ml, 2 mmol). The mixture was stirred at room temperature for 16 hours and poured into 100 ml of water. 1M HCl was added dropwise until pH=4. The precipitates were filtered, washed with water and dried in vacuo to give 2-[({5-[4-(2-fluoro-5-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)pyridin-2-yl]-1H-pyrrol-3-yl}carbonyl)amino]pentanedioic acid as white solid. Yield: 305 mg, 100%.

Workup

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

Sources & evidence

ORD record
ord-ccaaeaee3a284e469ca3314d8eef67c1
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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