Ethyl 3-bromo-2-oxocyclohexanecarboxylate → HCID 57780709, compound

HRID 2076015Notes

Reaction equation

HRID 2076015 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]([O:28][CH2:29][CH3:30])=[O:27])[C:21]1=O>C(O)C>[CH2:29]([O:28][C:26]([CH:22]1[C:21]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:20]=2[CH2:25][CH2:24][CH2:23]1)=[O:27])[CH3:30]

Participants

4

Reactant 2

HCID 121765Ethyl 3-bromo-2-oxocyclohexanecarboxylateHCID 71650841[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]thiourea

Product 1

HCID 57780709HCID 57780709, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (131 mg, 0.50 mmol) and of 2-bromo-6-(carbethoxy)-cyclohexanone (137 mg, 0.55 mmol) in ethanol (5 mL) was stirred at room temperature for 2 days and then heated to reflux under an atmosphere of nitrogen over night. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (180 mg, 87%) as a white solid. MS ISP (m/e): 413.3 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.28 (s, 1H), 7.66 (d, 1H), 7.64 (s, 1H), 7.21 (d, 1H), 7.11 (d, 1H), 7.01 (s, 1H), 4.10 (q, 2H), 3.76 (s, 3H), 3.66 (m, 1H), 2.62 (m, 2H), 2.14 (s, 3H), 1.68-2.09 (m, 4H), 1.19 (t, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux under an atmosphere of nitrogen over night
  3. customwas evaporated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-aecc0193e8714b099597acf8daae22dc
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

Loading…