Triethylamine → HCID 57829860, compound

HRID 1855359Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[C:11]([F:14])([F:13])[F:12])=[CH:4][CH:3]=1.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([NH:39][C:40]([NH2:42])=[NH:41])[CH:30]=[CH:31][C:32]=1[N:33]1[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]1.C(N(CC)CC)C>C(O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[N:41]=[C:40]([NH:39][C:29]3[CH:30]=[CH:31][C:32]([N:33]4[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]4)=[C:27]([O:26][CH3:25])[CH:28]=3)[N:42]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 78 °C

Procedure

A mixture of 1-(4-chloro-phenyl)-4,4,4-trifluoro-butane-1,3-dione (50 mg, 0.2 mmol), N-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-guanidine dinitrate (74 mg, 0.2 mmol), and triethylamine (0.14 mL, 1.0 mmol) in ethanol (0.5 mL) was heated to 78° C. for 18 h. The mixture was cooled, diluted with ethyl acetate (30 mL), and then washed with sat. sodium carbonate solution (5 mL) and with brine (5 mL). The organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residual material was purified by column chromatography on silica gel (5 g) using ethyl acetate/0-10% ethanol as eluent to give the title compound (10 mg, 11%) as light-yellow solid. Mp 202-204° C.

Workup

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

Sources & evidence

ORD record: ord-82a0fdbcad664fc1bf68503397512f7b
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962834B2

Reaction notes

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