HCID 67095889, compound → HCID 44195088, compound

HRID 2075991Notes

Reaction equation

HRID 2075991 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]([CH3:33])=[C:29]([C:34]([F:37])([F:36])[F:35])[CH:28]=2)[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][CH:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([C:34]([F:35])([F:37])[F:36])[CH:28]=4)[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 67095889HCID 67095889, compoundHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 44195088HCID 44195088, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (52 mg, 0.20 mmol) and of crude 6-bromo-2-(4-methyl-3-trifluoromethyl-phenyl)-cyclohexanone (70 mg, 0.21 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 (17 mg, 15%) as a pale-brown oil. MS ISP (m/e): 499.0 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.64 (s, 1H), 7.42 (s, 1H), 7.33 (s, 1H), 7.20 (s, 2H), 7.09 (d, 1H), 6.82 (s, 1H), 6.65 (d, 1H), 4.04 (m, 1H), 3.52 (s, 3H), 2.77 (m, 2H), 2.44 (s, 3H), 2.29 (s, 3H), 2.22 (m, 1H), 1.78-2.03 (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-27da0ec4cfea484b8c3e4fe22f431c8b
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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