Ethyl orthoformate → HCID 66869142, compound

HRID 250768Notes

Reaction equation

HRID 250768 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.[CH2:30](OC(OCC)OCC)[CH3:31]>>[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]=[C:30]1[CH3:31])[CH:21]([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 66868837HCID 66868837, compound

Product 1

HCID 66869142HCID 66869142, compoundYield 45%

Procedure

Heat a mixture of 1-(cyclohexyl)-4-phenyl-5-(3-(isobutylamino)-4-aminophenyl)-1H-imidazole (103 mg, 0.26 mmol) and 3 mL triethylorthoformate at 120° C. for 3 hours. Cool to room temperature and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 2:1 ethyl acetate:hexanes to provide the title compound (45%).

Workup

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

Sources & evidence

ORD record
ord-8a3d62e2a0ad4203bd720994f110109d
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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