Hydrochloric Acid → N-tert-butyl-2-(6-fluoro-1-(2,2,2-trifluoroethyl)-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246655Notes

Reaction equation

[C:1]([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]([F:31])([F:30])[F:29])[N:18]=3)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>CO>[C:1]([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]([F:29])([F:30])[F:31])[N:18]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of N-tert-Butyl-2-(6-fluoro-1-(2,2,2-trifluoroethyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (60 mg, 0.12 mmol) in 3 mL of methanol was added concentrated HCl (10 mL). The reaction mixture was heated to 50° C. and stirred overnight. The solvent was evaporated and the residue was triturated with tert-butyl methyl ether, filtered and dried to give N-tert-butyl-2-(6-fluoro-1-(2,2,2-trifluoroethyl)-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide as a yellow solid (30 mg, 58%). LCMS: (M+H)+=435; 1H NMR (300 MHz, DMSO): δ 12.86 (s, 1H), 9.04 (s, 1H), 8.52-8.47 (m, 1H), 8.41 (d, 1H, J=3.0 Hz), 7.89-7.83 (m, 2H), 7.26-7.23 (m, 1H), 5.62-5.53 (m, 2H), 1.51 (s, 9H).

Workup

customThe solvent was evaporated
customthe residue was triturated with tert-butyl methyl ether
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-303330b6547241bf9ed7da750127e86d
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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