Sodium hydroxide methanol → 3-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-phenyl-amino)-propionic acid

HRID 68188

Reaction equation

HRID 68188 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][N:6]([C:13]([C:15]1[CH:34]=[CH:33][C:18]2[N:19]([CH3:32])[C:20]([CH2:22][NH:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)=[N:21][C:17]=2[CH:16]=1)=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].CO>>[C:30]([C:27]1[CH:28]=[CH:29][C:24]([NH:23][CH2:22][C:20]2[N:19]([CH3:32])[C:18]3[CH:33]=[CH:34][C:15]([C:13]([N:6]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[CH2:5][CH2:4][C:3]([OH:35])=[O:2])=[O:14])=[CH:16][C:17]=3[N:21]=2)=[CH:25][CH:26]=1)#[N:31]

Participants

3

Reactant 2

HCID 23721981Sodium hydroxide methanolHCID 580694223-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-phenyl-amino)-propionic acid methyl ester

Product 1

HCID 580694233-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-phenyl-amino)-propionic acid

Conditions

Temperature
40 °C

Procedure

To a solution of the product of 1d (13.0 mmol) in 100 mL methanol sodium hydroxide (20.0 mmol) was added. The mixture was stirred for 2.5 hours at 40° C. and then evaporated to dryness. The remaining solid was stirred with 100 mL water and the pH was adjusted to about 6 with concentrated acetic acid. The precipitated product was isolated by filtration, washed with water and dried at 60° C.

Workup

  1. customevaporated to dryness
  2. stirringThe remaining solid was stirred with 100 mL water
  3. customThe precipitated product was isolated by filtration
  4. washwashed with water
  5. customdried at 60° C.

Sources & evidence

ORD record
ord-09cd8271a9db459ea2226cfcb13be652
Source dataset
uspto-grants-2014_09
Patent number
US08821871B2

Linked notes

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