Potassium Carbonate → HCID 90410457, compound

HRID 1527751Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[O:5][CH2:6][C:7]1[CH:11]=[CH:10][N:9]([CH3:12])[N:8]=1.C([O-])([O-])=O.[K+].[K+].[CH3:25][C:26]1[CH:31]=[C:30]([O:32][C:33]([F:36])([F:35])[F:34])[CH:29]=[CH:28][C:27]=1[CH2:37][NH2:38]>C(#N)C>[CH3:12][N:9]1[CH:10]=[CH:11][C:7]([CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([N+:16]([O-:18])=[O:17])=[C:2]([CH:3]=2)[NH:38][CH2:37][C:27]2[CH:28]=[CH:29][C:30]([O:32][C:33]([F:34])([F:35])[F:36])=[CH:31][C:26]=2[CH3:25])=[N:8]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-((3-fluoro-4-nitrophenoxy)methyl)-1-methyl-1H-pyrazole (143 mg, 0.573 mmol) in acetonitrile (10 mL) was added K2CO3 (317 mg, 2.3 mmol) followed by (2-methyl-4-(trifluoromethoxy)phenyl)methanamine (117 mg, 0.573 mmol). The mixture was stirred at 90° Celsius overnight. The reaction was cooled to RT and concentrated to dryness. The resulting residue was dissolved in DCM (50 mL) and washed with water (50 mL). The organic phase was concentrated to give the title compound. MS (ESI): mass calcd. for C20H19F3N4O4, 436.14; m/z found, 437 [M+H]+.

Workup

temperatureThe reaction was cooled to RT
concentrationconcentrated to dryness
dissolutionThe resulting residue was dissolved in DCM (50 mL)
washwashed with water (50 mL)
concentrationThe organic phase was concentrated

Sources & evidence

ORD record: ord-0fbef858a0634cc7881ad70b9ca93086
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09089569B2

Reaction notes

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