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

HRID 574107Notes

Reaction equation

HRID 574107 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-3dc6dff7ca26409cad567c98b0fe1eed
Source dataset
uspto-grants-2015_05
Patent number
US09034822B2

Reaction notes

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