6-Bromo-2-(4-chloro-phenyl)-cyclohexanone → [4-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-benzothiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

HRID 2076006Notes

Reaction equation

HRID 2076006 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]([NH2:18])=[S:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.Br[CH:20]1[C:25](=O)[CH:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)[CH2:23][CH2:22][CH2:21]1>C(O)C>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([CH:24]2[C:23]3[N:18]=[C:16]([NH:15][C:5]4[CH:6]=[CH:7][C:8]([N:9]5[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]5)=[C:3]([O:2][CH3:1])[CH:4]=4)[S:17][C:22]=3[CH2:21][CH2:20][CH2:25]2)=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 670962776-Bromo-2-(4-chloro-phenyl)-cyclohexanoneHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 57780681[4-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-benzothiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amineYield 19%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (50 mg, 0.19 mmol) and of crude 6-bromo-2-(4-chloro-phenyl)-cyclohexanone (74 mg, 0.26 mmol) in ethanol (2 mL) was heated to reflux under an atmosphere of nitrogen for 2 days. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (16 mg, 19%) as a brown gum. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.37 (s, 1H), 7.79 (s, 1H), 7.68 (d, 1H), 7.66 (s, 2H), 7.50 (d, 1H), 7.26 (d, 1H), 7.17 (d, 1H), 7.03 (s, 1H), 3.80 (m, 1H), 3.80 (s, 3H), 2.87 (m, 2H), 2.18 (m, 2H), 2.14 (s, 3H), 1.90 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-b83ed1cc2c964d75b6cf3220391743ef
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

Loading…