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 574106Notes

Reaction equation

HRID 574106 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-2c2d29bb97804cb9a6d7806598aa962a
Source dataset
uspto-grants-2015_05
Patent number
US09034822B2

Reaction notes

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