2-Phenylbutyric Acid → Methyl 3-methoxy-4-[6-(2-phenylbutanamido)benzimidazol-1-ylmethyl]benzoate

HRID 275142Notes

Reaction equation

HRID 275142 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]1([CH:19]([CH2:23][CH3:24])[C:20]([OH:22])=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH2:25][C:26]1[CH:27]=[CH:28][C:29]2[N:33]=[CH:32][N:31]([CH2:34][C:35]3[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][C:36]=3[O:45][CH3:46])[C:30]=2[CH:47]=1>ClCCl>[CH3:46][O:45][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][C:35]=1[CH2:34][N:31]1[C:30]2[CH:47]=[C:26]([NH:25][C:20](=[O:22])[CH:19]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:23][CH3:24])[CH:27]=[CH:28][C:29]=2[N:33]=[CH:32]1)[C:39]([O:41][CH3:42])=[O:40]

Participants

5

Reactant 3

HCID 70122-Phenylbutyric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 14763098Methyl 4-(6-aminobenzimidazol-1-ylmethyl)-3-methoxybenzoate

Product 1

HCID 23365891Methyl 3-methoxy-4-[6-(2-phenylbutanamido)benzimidazol-1-ylmethyl]benzoateYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1,1'-carbonyldiimidazole (0.23 g.) and 2-phenylbutyric acid (0.22 g.) in dichloromethane (3 ml.) was heated under reflux for 30 minutes and then treated with a solution of (J) (0.41 g.) in dichloromethane (3 ml.). The mixture was heated under reflux for an additional 10 minutes and then diluted with dichloromethane. This mixture was washed successively with 10% v/v hydrochloric acid, water, and brine, then dried (MgSO4) and evaporated. The resultant residue was purified by flash chromatography on a 5×25 cm. silica gel column using 3:97 v/v methanol:dichloromethane as the eluent to give the title compound (0.15 g., 25%): partial NMR: 2.0(br m,2H, CH3CH2), 3.4(t,1H, CH2CH), 7.3(s,5H, Ar).

Workup

  1. temperatureunder reflux for 30 minutes
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for an additional 10 minutes
  4. washThis mixture was washed successively with 10% v/v hydrochloric acid, water, and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe resultant residue was purified by flash chromatography on a 5×25 cm

Sources & evidence

ORD record
ord-b0b328dfec2840b3bb3cedab37085dba
Source dataset
uspto-grants-1995_02
Patent number
US05391758

Reaction notes

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