Trimethyl orthoformate → HCID 66869159, compound

HRID 250767Notes

Reaction equation

HRID 250767 reaction equation
[CH:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([NH:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH:13]=3)=[C:10]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:9]=[CH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:30](OC)(OC)OC>>[CH2:20]([N:19]1[C:14]2[CH:13]=[C:12]([C:11]3[N:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[CH:8]=[N:9][C:10]=3[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:17]=[CH:16][C:15]=2[N:18]=[CH:30]1)[CH:21]([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 66868837HCID 66868837, compound

Product 1

HCID 66869159HCID 66869159, compoundYield 73%

Procedure

Heat a mixture of 1-(cyclohexyl)-4-phenyl-5-(3-(isobutylamino)-4-aminophenyl)-1H-imidazole (83 mg, 0.21 mmol) and 3 mL trimethyl orthoformate at 120° C. for 6 hours. Cool to room temperature and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 3:1 ethyl acetate:hexanes to provide the title compound (73%).

Workup

  1. temperatureHeat
  2. concentrationconcentrate under reduced pressure
  3. washeluting with 3:1 ethyl acetate

Sources & evidence

ORD record
ord-bdc54162d2ac4ede81289ccb29531eb8
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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