Water → N-Cyclobutyl-N-{1-[2-(4-fluorophenyl)pyridin-4-yl]ethyl}-1-methyl-1H-imidazole-4-carboxamide

HRID 1026766Notes

Reaction equation

HRID 1026766 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]([NH:16][CH:17]3[CH2:20][CH2:19][CH2:18]3)[CH3:15])[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:21][N:22]1[CH:26]=[C:25]([C:27](Cl)=[O:28])[N:24]=[CH:23]1.C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[CH:17]1([N:16]([CH:14]([C:12]2[CH:11]=[CH:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:13]=2)[CH3:15])[C:27]([C:25]2[N:24]=[CH:23][N:22]([CH3:21])[CH:26]=2)=[O:28])[CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 513419821-Methyl-1H-imidazole-4-carbonyl chlorideHCID 86690484N-{1-[2-(4-Fluorophenyl)pyridin-4-yl]ethyl}cyclobutaneamine

Product 1

HCID 86690493N-Cyclobutyl-N-{1-[2-(4-fluorophenyl)pyridin-4-yl]ethyl}-1-methyl-1H-imidazole-4-carboxamideYield 85.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N-{1-[2-(4-fluorophenyl)pyridin-4-yl]ethyl}cyclobutaneamine (100 mg), 1-methyl-1H-imidazole-4-carbonyl chloride (110 mg) and triethylamine (100 mg) in chloroform (5 mL) was stirred at room temperature overnight. Water was added thereto, followed by extraction with chloroform, and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=75:25-0:100) to afford the title compound (120 mg).

Workup

  1. extractionfollowed by extraction with chloroform
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=75:25-0:100)

Sources & evidence

ORD record
ord-fba5a650c5874ab7be5658fd73840216
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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