2-Bromo-6-phenylcyclohexanone → [3-Fluoro-4-(4-methyl-imidazol-1-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

HRID 2075981Notes

Reaction equation

HRID 2075981 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:14][C:15]([NH2:17])=[S:16])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]1.Br[CH:19]1[CH2:24][CH2:23][CH2:22][CH:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]1=O>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:14][C:15]2[S:16][C:27]3[CH2:28][CH2:29][CH2:30][CH:25]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:19][CH:20]=4)[C:26]=3[N:17]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632602[3-Fluoro-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea

Product 1

HCID 57392070[3-Fluoro-4-(4-methyl-imidazol-1-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amineYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [3-fluoro-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (125 mg, 0.50 mmol) and of 2-bromo-6-phenyl-cyclohexanone (253 mg, 1.00 mmol) in ethanol (4 mL) was stirred at room temperature for 30 minutes and then heated for two days to reflux under an atmosphere of nitrogen. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was purified on silica gel using dichloromethane and then dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (200 mg, 99%) as a white solid. MS ISP (m/e): 405.4 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.40 (s, 1H), 7.73 (s, 1H), 7.67 (d, 1H), 7.38 (t, 1H), 7.32 (t, 2H), 7.10-7.21 (m, 4H), 4.04 (m, 1H), 2.70 (m, 2H), 2.13 (s, 3H), 2.11 (m, 1H), 1.70-1.89 (m, 3H).

Workup

  1. temperatureheated for two days
  2. temperatureto reflux under an atmosphere of nitrogen
  3. customwas evaporated under reduced pressure
  4. customthe residue was purified on silica gel

Sources & evidence

ORD record
ord-79ff53526ccd4901a4ca80573bbaee28
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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