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

HRID 574110Notes

Reaction equation

HRID 574110 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-ba2e142f1b07482f96a038e04964f1d0
Source dataset
uspto-grants-2015_05
Patent number
US09034822B2

Reaction notes

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