Ammonia → HCID 86716189, compound

HRID 512164Notes

Reaction equation

HRID 512164 reaction equation
C([O:3][C:4]([C:6]1([N:14]2[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]2)[CH2:11][CH2:10][C:9]([F:13])([F:12])[CH2:8][CH2:7]1)=O)C.[NH3:20]>CO>[F:12][C:9]1([F:13])[CH2:10][CH2:11][C:6]([N:14]2[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]2)([C:4]([NH2:20])=[O:3])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86716190HCID 86716190, compound

Product 1

HCID 86716189HCID 86716189, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4,4-Difluoro-1-(4-methyl-imidazol-1-yl)-cyclohexanecarboxylic acid ethyl ester (199 mg, 0.731 mmol was dissolved in 7 M ammonia in methanol (5 mL) and stirred for 72 hours. The sample was concentrated and the residue was purified by flash column chromatography on silica gel (eluding w a gradient elution from heptane to AcOEt to 5% Et3N/10% MeOH185% AcOEt) to give the title compound (84 mg, 45%) 1H NMR (CDCl3 500 MHz): 6 ppm 7.64 (s, 1H), 6.82 (s, 1H), 5.17 (m, 2H), 2.68 (m, 2H), 2.41 (m, 2H), 2.30 (s, 3H), 2.23 (m, 2H), 1.85 (m, 2H).

Workup

  1. concentrationThe sample was concentrated
  2. customthe residue was purified by flash column chromatography on silica gel (
  3. washa gradient elution from heptane to AcOEt to 5% Et3N/10% MeOH185% AcOEt)

Sources & evidence

ORD record
ord-a7f53de163a64783a91d6542093745be
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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