Sodium Hydroxide → N-[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-beta-alanine

HRID 68191Notes

Reaction equation

HRID 68191 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:38])[CH2:7][CH2:8][N:9]([C:16]([C:18]1[CH:37]=[CH:36][C:21]2[N:22]([CH3:35])[C:23]([CH2:25][NH:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=3)=[N:24][C:20]=2[CH:19]=1)=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)C>C(O)C.O>[C:33]([C:30]1[CH:31]=[CH:32][C:27]([NH:26][CH2:25][C:23]2[N:22]([CH3:35])[C:21]3[CH:36]=[CH:37][C:18]([C:16]([N:9]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=4)[CH2:8][CH2:7][C:6]([OH:38])=[O:5])=[O:17])=[CH:19][C:20]=3[N:24]=2)=[CH:28][CH:29]=1)#[N:34]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11627749Ethyl 3-(((2-(((4-cyanophenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)pyridin-2-ylamino)propionate

Product 1

HCID 18412686N-[[2-[[(4-Cyanophenyl)amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-beta-alanine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of sodium hydroxide (50.0 mmol) in 500 mL ethanol and 50 mL water was added 3-({2-[(4-Cyano-phenylamino)-methyl]-1-methyl-1H-benzoimidazole-5-carbonyl}-pyridin-2-yl-amino)-propionic acid ethyl ester (41.4 mmol). The mixture was stirred at room temperature for three hours, then ca. 350 mL ethanol were distilled off, ca. 100 mL water was added and the pH was adjusted to 6. Then diethylether (50 mL) was added and the mixture stirred over night. The product was isolated by filtration and used without further purification.

Workup

  1. distillationca. 350 mL ethanol were distilled off
  2. additionca. 100 mL water was added
  3. additionThen diethylether (50 mL) was added
  4. stirringthe mixture stirred over night
  5. customThe product was isolated by filtration
  6. customused without further purification

Sources & evidence

ORD record
ord-02c12e876b0d4c54872a87cf3dfdf4d9
Source dataset
uspto-grants-2014_09
Patent number
US08821871B2

Reaction notes

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