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

HRID 2076001Notes

Reaction equation

HRID 2076001 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][CH:30]=[CH:29][C:28]=2[Cl:33])[CH2:23][CH2:22][CH2:21]1>C(O)C>[Cl:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH:24]1[C:23]2[N:18]=[C:16]([NH:15][C:5]3[CH:6]=[CH:7][C:8]([N:9]4[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]4)=[C:3]([O:2][CH3:1])[CH:4]=3)[S:17][C:22]=2[CH2:21][CH2:20][CH2:25]1

Participants

4

Reactant 2

HCID 670959316-Bromo-2-(2-chloro-phenyl)-cyclohexanoneHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 44195182[4-(2-Chloro-phenyl)-4,5,6,7-tetrahydro-benzothiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amineYield 46.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (69 mg, 0.26 mmol) and of crude 6-bromo-2-(2-chloro-phenyl)-cyclohexanone (79 mg, 0.28 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 reversed preparative HPLC using acetonitril/water (0.1% formic acid) to yield the title compound (55 mg, 46%) as an off-white solid. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.77 (s, 1H), 7.46 (s, 1H), 7.35 (m, 1H), 7.13 (m, 2H), 7.08 (d, 1H), 6.96 (m, 1H), 6.85 (s, 1H), 6.68 (d, 1H), 4.53 (m, 1H), 3.54 (s, 3H), 2.77 (m, 2H), 2.33 (s, 3H), 2.24 (m, 1H), 1.80-1.99 (m, 3H).

Workup

  1. temperatureto reflux under an atmosphere of nitrogen for 2 days
  2. customwas evaporated under reduced pressure
  3. customthe residue was purified by reversed preparative HPLC

Sources & evidence

ORD record
ord-2fe381938e9c4588ac5972738feb0af4
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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