Cyclohexene → HCID 46831763, compound

HRID 530305Notes

Reaction equation

HRID 530305 reaction equation
C([N:8]1[N:12]=[N:11][C:10]([C:13]2[CH:14]=[C:15]([C:19]3[N:20]=[CH:21][N:22]([C:24]([N:26]([CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)[CH3:27])=[O:25])[CH:23]=3)[CH:16]=[CH:17][CH:18]=2)=[N:9]1)C1C=CC=CC=1.C1CCCCC=1>[Pd]>[N:11]1[NH:12][N:8]=[N:9][C:10]=1[C:13]1[CH:14]=[C:15]([C:19]2[N:20]=[CH:21][N:22]([C:24]([N:26]([CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH3:27])=[O:25])[CH:23]=2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 8079CyclohexeneHCID 66682834HCID 66682834, compound

Product 1

HCID 46831763HCID 46831763, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 4-(3-(2-benzyl-2H-tetrazol-5-yl)phenyl)-N-cyclohexyl-N-methyl-1H-imidazole-1-carboxamide (256 mg, 0.58 mmol), 10% palladium on carbon (30.9 mg, 0.029 mmol) and cyclohexene (1.175 ml, 11.6 mmol) was heated at 80° C. in a sealed tube. Then the reaction was cooled to room temperature, filtered through a celite pad and evaporated to dryness. The remaining oil was purified by chromatography over silica using a mixture of dichloromethane/methanol (90:10). Homogenous fractions were pooled and evaporated and the residual oil was crystallised from diethyl ether to give the product as an off-white powder, (45 mg, 21%).

Workup

  1. temperatureThen the reaction was cooled to room temperature
  2. filtrationfiltered through a celite pad
  3. customevaporated to dryness
  4. customThe remaining oil was purified by chromatography over silica using
  5. additiona mixture of dichloromethane/methanol (90:10)
  6. customevaporated
  7. customthe residual oil was crystallised from diethyl ether

Sources & evidence

ORD record
ord-a8dafbd98a6c47c3b0826dd95874dafb
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

Loading…