Cyclohexylamine → HCID 24906065, compound

HRID 730059Notes

Reaction equation

HRID 730059 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[C:10]([S:20][CH3:21])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH:22]1([NH2:28])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH:22]1([NH:28][C:2]2[CH:7]=[C:6]([C:8]3[N:9]=[C:10]([S:20][CH3:21])[NH:11][C:12]=3[C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH:5]=[CH:4][N:3]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 7965CyclohexylamineHCID 44339273HCID 44339273, compound

Product 1

HCID 24906065HCID 24906065, compound

Procedure

2-Fluoro-4-[5-(4-fluorophenyl)-2-methylsulfanyl-1 H-imidazol-4-yl]pyridine (1.2 g, 4 mmol), which had been weighed out into a 25 ml one-necked flask which had been flushed with argon beforehand, was suspended in cyclohexylamine (3.97 g, 0.04 mol), covered with argon and then heated with reflux of the amine, in an oil bath at a temperature of 160° C., for 48 h. The brown suspension is allowed to cool to RT. 30 ml of Na citrate solution (10% strength citric acid solution pH 5 with conc. NaOH) are then added, and the mixture is stirred for 10 min. and extracted twice with 30 ml of ethyl acetate.

Workup

  1. customwhich had been flushed with argon beforehand
  2. temperatureheated
  3. extractionextracted twice with 30 ml of ethyl acetate

Sources & evidence

ORD record
ord-d98fc85b152e4050ab8f42407870b332
Source dataset
uspto-grants-2009_09
Patent number
US07582660B2

Reaction notes

Loading…