Trifluoroacetic acid → 2-(Isoquinolin-7-ylamino)-N-(4-pentafluoroethyl-phenyl)-nicotinamide

HRID 887675Notes

Reaction equation

F[C:2]1[N:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1)=[O:5].[NH2:24][C:25]1[CH:34]=[C:33]2[C:28]([CH:29]=[CH:30][N:31]=[CH:32]2)=[CH:27][CH:26]=1.C(O)(C(F)(F)F)=O>CC(O)(C)C>[CH:32]1[C:33]2[C:28](=[CH:27][CH:26]=[C:25]([NH:24][C:2]3[N:23]=[CH:22][CH:21]=[CH:20][C:3]=3[C:4]([NH:6][C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=3)=[O:5])[CH:34]=2)[CH:29]=[CH:30][N:31]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 2-fluoro-N-(4-pentafluoroethyl-phenyl)-nicotinamide (112 mg) and 7-aminoisoquinoline (40 mg) in t-BuOH (0.5 mL) was added TFA (94 μL). The resulting mixture was stirred for 24 h at 90° C., cooled to RT and purified by flash chromatography (4:1:0.1; MeOH/CH2Cl2/MeOH) to give the title compound as a yellow solid. MS (ES+): 459 (M+H)+. Calc'd for C23H15F5N4O—458.12.

Workup

temperaturecooled to RT
custompurified by flash chromatography (4:1:0.1; MeOH/CH2Cl2/MeOH)

Sources & evidence

ORD record: ord-c64a1a69a83e44b7a6154a887cce14fd
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247430B2

Reaction notes

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