Trifluoroacetic acid → HCID 71280056, compound

HRID 246457Notes

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][CH2:28][N:29]([CH3:31])[CH3:30])[N:18]=3)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[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][CH2:28][N:29]([CH3:31])[CH3:30])[N:18]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

N-tert-Butyl-2-(1-(2-(dimethylamino)ethyl)-6-fluoro-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.085 g, 153 μmol) was placed in a sealed tube and dissolved in dichloromethane (2 mL). Trifluoroacetic acid (1.75 g, 1.18 mL, 15.3 mmol) was added and the tube sealed and the mixture heated at to 80° C. After 15 h the mixture was cooled and then concentrated in vacuo. The residue was crystallized from dichloromethane/methanol and cyclohexane to give N-tert-butyl-2-(1-(2-(dimethylamino)ethyl)-6-fluoro-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (38 mg, 89.7 μmol, 58.5%) as a white powder. MS (M+H)+=424; 1H NMR (CDCl3) δ: 9.07 (s, 1H), 8.42-8.50 (m, 1H), 8.24 (s, 1H), 7.33-7.41 (m, 1H), 7.02 (s, 1H), 4.88 (s, 2H), 3.68-3.79 (m, 2H), 2.85 (s, 7H), 1.55 (s, 6H).

Workup

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

Sources & evidence

ORD record: ord-790855cbf778478bac3dfbec887800c9
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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