Potassium Carbonate → HCID 57829752, compound

HRID 1855466Notes

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.O=[C:28]([CH2:34][C:35](=O)[CH3:36])[C:29]([O:31][CH2:32][CH3:33])=[O:30].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:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:34]=[C:35]([CH3:36])[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

Conditions

Temperature: 170 °C

Procedure

A mixture of N-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-guanidine dinitrate (371 mg, 1.0 mmol), ethyl 2,4-dioxo-pentanoate (158 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 (50 mL), and then washed with water (20 mL) and with brine (20 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/0-10% methanol as eluent to give the title compound (229 mg, 62%) as a yellow solid. MS ISP (m/e): 368.2 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.04 (d, 1H), 7.64 (s, 1H), 7.40 (s, 1H), 7.34 (s, 1H), 7.17 (d, 1H), 6.98 (dd, 1H), 6.87 (s, 1H), 4.46 (q, 2H), 3.91 (s, 3H), 2.54 (s, 3H), 2.30 (s, 3H), 1.43 (t, 3H).

Workup

temperatureThe mixture was cooled
washwashed with water (20 mL) and with brine (20 mL)
dry with materialThe organic layer was dried over sodium sulfate
customevaporated under reduced pressure
customThe residual material was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-71b8047a6ca04d49b58f45e855b427f6
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962834B2

Reaction notes

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