HCID 67096141, compound → HCID 44195091, compound

HRID 2075999Notes

Reaction equation

HRID 2075999 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]=[C:31]([CH3:33])[CH:30]=[CH:29][C:28]=2[CH3:34])[CH2:23][CH2:22][CH2:21]1>C(O)C>[CH3:34][C:28]1[CH:29]=[CH:30][C:31]([CH3:33])=[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 67096141HCID 67096141, compoundHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 44195091HCID 44195091, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (72 mg, 0.27 mmol) and of crude 6-bromo-2-(2,5-dimethyl-phenyl)-cyclohexanone (81 mg, 0.29 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 (11 mg, 9%) as an off-white solid. MS ISP (m/e): 445.3 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.60 (s, 1H), 7.35 (s, 1H), 7.09 (d, 1H), 7.03 (d, 1H), 2.34 (s, (d, 1H), 6.82 (s, 1H), 6.69 (s, 1H), 6.62 (d, 1H), 4.21 (m, 1H), 3.53 (s, 3H), 2.78 (m, 2H), 2.34 (s, 3H), 2.28 (s, 3H), 2.23 (s, 3H), 2.15 (m, 1H), 1.75-2.05 (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-3df8a1732e6e4677aa49bc2c41d96924
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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