Potassium Carbonate → HCID 57829859, compound

HRID 1855463Notes

Reaction equation

HRID 1855463 reaction equation
[N+]([O-])(O)=O.[N+]([O-])(O)=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:23][C:24]([NH2:26])=[NH:25])[CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]1.CN(C)[CH:29]=[CH:30][C:31](=O)[C:32]([O:34][CH2:35][CH3:36])=[O:33].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)(=O)C>[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:23][C:24]2[N:26]=[C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:30]=[CH:29][N:25]=2)[CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2777802Ethyl 4-(dimethylamino)-2-oxo-but-3-enoateHCID 178493228HCID 178493228, compound

Product 1

HCID 57829859HCID 57829859, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of N-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]guanidine dinitrate (298 mg, 0.80 mmol), ethyl 4-dimethylamino-2-oxo-but-3-enoate (171 mg, 1.0 mmol) and potassium carbonate (69 mg, 0.5 mmol) in ethanol (2 mL) was heated in a sealed tube in a microwave oven to 170° C. for 0.5 h. The mixture was cooled, diluted with ethyl acetate (30 mL), and then washed with saturated sodium carbonate solution (10 mL) and with brine (10 mL). The organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residual material was purified by chromatography on silica gel using dichloromethane/0-20% methanol as eluent to give the title compound (96 mg, 34%) as a pale-yellow solid. MS ISP (m/e): 354.2 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.67 (d, 1H), 7.91 (d, 1H), 7.64 (s, 1H), 7.45 (s, 1H), 7.44 (d, 1H), 7.19 (d, 1H), 7.02 (dd, 1H), 6.88 (s, 1H), 4.47 (q, 2H), 3.91 (s, 3H), 2.30 (s, 3H), 1.44 (t, 3H).

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with saturated sodium carbonate solution (10 mL) and with brine (10 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe residual material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f758b0fc0aba441cb50cfe54a71e64a7
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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