Potassium Carbonate → HCID 57829735, compound

HRID 1855516Notes

Reaction equation

HRID 1855516 reaction equation
[N+]([O-])(O)=O.[F:5][C:6]1[CH:7]=[C:8]([NH:18][C:19]([NH2:21])=[NH:20])[CH:9]=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1.[CH3:22][CH:23]([CH3:34])[C:24](=O)[CH2:25][C:26](=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(OCC)(=O)C>[F:5][C:6]1[CH:7]=[C:8]([NH:18][C:19]2[N:21]=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:25]=[C:24]([CH:23]([CH3:22])[CH3:34])[N:20]=2)[CH:9]=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([CH3:17])[N:14]=[CH:13]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 3017501Ethyl 5-methyl-2,4-dioxohexanoateHCID 178429954HCID 178429954, compound

Product 1

HCID 57829735HCID 57829735, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of N-[3-fluoro-4-(4-methyl-imidazol-1-yl)-phenyl]-guanidine nitrate (719 mg, 2.0 mmol), ethyl 5-methyl-2,4-dioxo-hexanoate (372 mg, 2.0 mmol) and potassium carbonate (138 mg, 1.0 mmol) in ethanol (5 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 (153 mg, 20%) as a light yellow solid. MS ISP (m/e): 384.3 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): 8 (ppm)=8.11 (dd, 1H), 7.68 (s, 1H), 7.47 (s, 1H), 7.38 (s, 1H), 7.25-7.30 (2H), 6.94 (s, 1H), 4.48 (q, 2H), 3.05 (m, 1H), 2.31 (s, 3H), 1.46 (t, 3H), 1.36 (d, 6H).

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with water (20 mL) and with brine (20 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-f0f48933d01b49e6be47602a87f2c335
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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