HCID 67096052, compound → HCID 44193751, compound

HRID 2076024Notes

Reaction equation

HRID 2076024 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[CH2:25][CH2:24][CH2:23][CH:22]([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[C:28]([Cl:33])[CH:27]=2)[C:21]1=O>C(O)C>[Cl:32][C:30]1[CH:31]=[C:26]([CH:22]2[C:21]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:20]=3[CH2:25][CH2:24][CH2:23]2)[CH:27]=[C:28]([Cl:33])[CH:29]=1

Participants

4

Reactant 2

HCID 67096052HCID 67096052, compoundHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 44193751HCID 44193751, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (58 mg, 0.22 mmol) and of crude 2-bromo-6-(3,5-dichloro-phenyl)-cyclohexanone (75 mg, 0.23 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 (30 mg, 28%) as a yellow solid. MS ISP (m/e): 485.3/487.3 (100/72) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.64 (s, 1H), 7.35 (s, 1H), 7.20 (s, 1H), 7.11 (d, 1H), 7.04 (s, 2H), 6.84 (s, 1H), 6.69 (d, 1H), 3.98 (m, 1H), 3.63 (s, 3H), 2.75 (m, 2H), 2.30 (s, 3H), 2.22 (m, 1H), 1.83 (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-9f72648cd68c43cbbd20515d7db688fa
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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