Ammonium formate → N-Methyl-N-(4-(4-(1-(imidazol-2-ylmethyl)-1H-benzimidazole-2-carbonyl)piperidin-1-yl)-2-phenylbutyl)benzamide

HRID 379474

Reaction equation

HRID 379474 reaction equation
[CH3:1][N:2]([CH2:11][CH:12]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]([C:23]2[N:27]([CH2:28][C:29]3[N:30](CC4C=CC=CC=4)[CH:31]=[CH:32][N:33]=3)[C:26]3[CH:41]=[CH:42][CH:43]=[CH:44][C:25]=3[N:24]=2)=[O:22])[CH2:17][CH2:16]1)[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][N:2]([CH2:11][CH:12]([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([C:21]([C:23]2[N:27]([CH2:28][C:29]3[NH:33][CH:32]=[CH:31][N:30]=3)[C:26]3[CH:41]=[CH:42][CH:43]=[CH:44][C:25]=3[N:24]=2)=[O:22])[CH2:19][CH2:20]1)[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 21697470N-methyl-N-(4-(4-(1-(1-benzylimidazol-2-ylmethyl)-1H-benzimidazole-2-carbonyl)piperidin-1-yl)-2-phenylbutyl)benzamide

Product 1

HCID 21697366N-Methyl-N-(4-(4-(1-(imidazol-2-ylmethyl)-1H-benzimidazole-2-carbonyl)piperidin-1-yl)-2-phenylbutyl)benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Combine N-methyl-N-(4-(4-(1-(1-benzylimidazol-2-ylmethyl)-1H-benzimidazole-2-carbonyl)piperidin-1-yl)-2-phenylbutyl)benzamide (5 mmol) and 10% palladium-on-carbon (1.5 g) in methanol (50 mL). Add anhydrous ammonium formate (25 mmol). Heat to reflux. After 18 hours, filter, rinse with dichloromethane, and evaporate the filtrate in vacuo to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. filtrationfilter
  3. washrinse with dichloromethane
  4. customevaporate the filtrate in vacuo

Sources & evidence

ORD record
ord-7caf438962724a72873b633243986422
Source dataset
uspto-grants-2001_10
Patent number
US06297259B1

Linked notes

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