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

HRID 2075989Notes

Reaction equation

HRID 2075989 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)[C:24]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=2)([CH2:27][CH2:28][CH3:29])[CH2:23][CH2:22][CH2:21]1>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[S:17][C:22]3[CH2:21][CH2:20][CH2:25][C:24]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=4)([CH2:27][CH2:28][CH3:29])[C:23]=3[N:18]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

4

Reactant 2

HCID 670961976-Bromo-2-(3-methoxy-phenyl)-2-propyl-cyclohexanoneHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 57780713[3-Methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-[4-(3-methoxy-phenyl)-4-propyl-4,5,6,7-tetrahydro-benzothiazol-2-yl]-amineYield 3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (100 mg, 0.38 mmol) and of crude 6-bromo-2-(3-methoxy-phenyl)-2-propyl-cyclohexanone (126 mg, 0.39 mmol) in ethanol (5 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 (5 mg, 3%) as a yellow solid. MS ISP (m/e): 489.3 (100) [(M+H)−]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.64 (s, 1H), 7.58 (d, 1H), 7.12-7.19 (m, 2H), 6.68-6.89 (m, 5H), 3.76 (s, 6H), 2.67 (m, 2H), 2.29 (s, 3H), 1.05-2.16 (m, 8H), 0.89 (t, 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-623d0a981fce4a0a82683b0c3a956111
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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