Trifluoroacetic acid → 2-(6-fluoro-1-(2-morpholino-2-oxoethyl)-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246458Notes

Reaction equation

C([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([C:17]3[C:25]4[C:20](=[CH:21][C:22]([F:26])=[CH:23][CH:24]=4)[N:19]([CH2:27][C:28]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[O:29])[N:18]=3)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:26][C:22]1[CH:21]=[C:20]2[C:25]([C:17]([C:14]3[N:15]=[C:16]4[C:8]([C:6]([NH2:5])=[O:7])=[CH:9][NH:10][C:11]4=[N:12][CH:13]=3)=[N:18][N:19]2[CH2:27][C:28]([N:30]2[CH2:31][CH2:32][O:33][CH2:34][CH2:35]2)=[O:29])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

N-tert-Butyl-2-(6-fluoro-1-(2-morpholino-2-oxoethyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (42 mg, 68.9 μmol) was placed in a sealed tube and dissolved in dichloromethane (2 mL). Trifluoroacetic acid (785 mg, 531 μL, 6.89 mmol) was added and the tube was sealed and the mixture heated at to 80° C. After 15 h the mixture was cooled and concentrated in vacuo. Recrystallization from dichloromethane/methanol and cyclohexane gave 2-(6-fluoro-1-(2-morpholino-2-oxoethyl)-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (7 mg, 16.5 μmol, 24.0%) as a white powder. MS (M−H)−=422; 1H NMR (DMSO-d6) δ: 8.42 (s, 1H), 7.72 (dd, J=8.9, 5.1 Hz, 1H), 7.65 (s, 1H), 6.73 (d, J=9.4 Hz, 1H), 6.37-6.47 (m, 1H), 4.82 (s, 2H), 2.89-3.09 (m, 6H), 2.82 (d, J=4.9 Hz, 2H).

Workup

customthe tube was sealed
temperatureAfter 15 h the mixture was cooled
concentrationconcentrated in vacuo
customRecrystallization from dichloromethane/methanol and cyclohexane

Sources & evidence

ORD record: ord-3b3c2ef2a75c44edb84df0fd245efa99
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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