Acetonitrile → HCID 58999043, compound

HRID 2105766Notes

Reaction equation

HRID 2105766 reaction equation
N1([NH:7][C:8]([C:10]2[N:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[NH:13][C:14]=2[CH3:15])=[O:9])CCCCC1.C[C:24]([O-])([CH3:26])[CH3:25].[K+].Br[CH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.[C:37](#N)C>>[CH2:37]([NH:7][C:8]([C:10]1[N:11]=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[N:13]([CH2:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[C:14]=1[CH3:15])=[O:9])[CH2:25][CH2:24][CH3:26]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 137636Cyclohexane, (bromomethyl)-HCID 23665647Potassium tert-butoxideHCID 68838889HCID 68838889, compound

Product 1

HCID 58999043HCID 58999043, compound

Procedure

To a suspension of 90 mg of 2-(2-chloro-phenyl)-5-methyl-1H-imidazole-4-carboxylic acid piperidin-1-ylamide in 4 ml of acetonitrile was added 35 mg of potassium tert-butylate and the reaction mixture was stirred at room temperature for 2 minutes. After such time, 0.04 ml of (bromomethyl)cyclohexane was added and the reaction mixture was stirred at 80° C. for 28 hours under argon atmosphere. The reaction mixture was then concentrated in vacuo and purified by column chromatography (SiO2, Heptane/EtOAC:1/1) to give 64 mg of the title compound as a pale yellow solid, MS (ISP) 415.3 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred at 80° C. for 28 hours under argon atmosphere
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. custompurified by column chromatography (SiO2, Heptane/EtOAC:1/1)

Sources & evidence

ORD record
ord-d52f60324a674bbe8b7d668c62d0b1ac
Source dataset
uspto-grants-2009_08
Patent number
US07579369B2

Reaction notes

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