HCID 67096234, compound → HCID 44195183, compound

HRID 2076004Notes

Reaction equation

HRID 2076004 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])=[C:29]([C:34]([F:37])([F:36])[F:35])[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][C:29]=1[C:34]([F:35])([F:36])[F:37]

Participants

4

Reactant 2

HCID 67096234HCID 67096234, compoundHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 44195183HCID 44195183, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (39 mg, 0.15 mmol) and of crude 6-bromo-2-(4-chloro-3-trifluoromethyl-phenyl)-cyclohexanone (53 mg, 0.16 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 (22 mg, 29%) as a yellow gum. MS ISP (m/e): 518.8/520.9 (100/36) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.62 (s, 1H), 7.56 (s, 1H), 7.41 (d, 2H), 7.30 (s, 1H), 7.10 (d, 1H), 6.83-6.89 (m, 2H), 6.67 (d, 1H), 4.05 (m, 1H), 3.55 (s, 3H), 2.75 (m, 2H), 2.29 (s, 3H), 2.22 (m, 1H), 1.78-2.05 (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-5c02bf993349410f99ff6cd54f25bad0
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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