3-({3-[2-(4-Cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-phenyl-amino)-propionic acid methyl ester → 3-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-phenyl-amino)-propionic acid methyl ester

HRID 449742Notes

Reaction equation

HRID 449742 reaction equation
[CH3:1][O:2][C:3](=[O:36])[CH2:4][CH2:5][N:6]([C:13](=[O:35])[C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH3:21])=[C:16]([NH:22][C:23](=O)[CH2:24][NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=2)[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:36])[CH2:4][CH2:5][N:6]([C:13]([C:14]1[CH:19]=[CH:18][C:17]2[N:20]([CH3:21])[C:23]([CH2:24][NH:25][C:26]3[CH:27]=[CH:28][C:29]([C:32]#[N:33])=[CH:30][CH:31]=3)=[N:22][C:16]=2[CH:15]=1)=[O:35])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 1

HCID 667063283-({3-[2-(4-Cyano-phenylamino)-acetylamino]-4-methylamino-benzoyl}-phenyl-amino)-propionic acid methyl ester

Product 1

HCID 580694223-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-phenyl-amino)-propionic acid methyl esterYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of 1c (22.6 mmol) in 100 mL concentrated acetic acid was heated to reflux for one hour. The solution was then evaporated to dryness, the remaining solid triturated with water and under stirring the pH was adjusted to about 8-9. The crude product was isolated through extraction with ethyl acetate and purified by chromatography on silica gel (eluent: dichloromethane/ethanol 1:1).

Workup

  1. temperatureto reflux for one hour
  2. customThe solution was then evaporated to dryness
  3. customthe remaining solid triturated with water

Sources & evidence

ORD record
ord-60800b91261a4df8b54b27e720d02a1b
Source dataset
uspto-grants-2013_07
Patent number
US08486398B2

Reaction notes

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