Trifluoroacetic acid → HCID 178461841, compound

HRID 2043415Notes

Reaction equation

FC(F)(F)C(O)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]3[CH:28]=[CH:27][N:26](COCC[Si](C)(C)C)[N:25]=3)[CH:21]=[C:20]([NH:37][C:38]3[CH:43]=[N:42][CH:41]=[CH:40][N:39]=3)[N:19]=2)[CH3:16])=[CH:11][CH:10]=1>O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([NH:17][C:18]2[CH:23]=[C:22]([C:24]3[CH:28]=[CH:27][NH:26][N:25]=3)[CH:21]=[C:20]([NH:37][C:38]3[CH:43]=[N:42][CH:41]=[CH:40][N:39]=3)[N:19]=2)[CH3:16])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixed solvent of 3 ml of trifluoroacetic acid and 0.3 ml of water was added to 95 mg of (S)—N2-[1-(4-fluorophenyl)ethyl]-N6-(pyrazin-2-yl)-4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-3-yl)pyridine-2,6-diamine obtained by Step 6, and the mixture was stirred at 60° C. for 1 hour. The solvent was distilled off under reduced pressure, and then the obtained residue was diluted with water and alkalified with a saturated aqueous solution of sodium bicarbonate. The reaction solution was subjected to extraction with ethyl acetate, and the organic layer was washed with water and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 20 mg of the objective compound as pale yellow powder.

Workup

distillationThe solvent was distilled off under reduced pressure
additionthe obtained residue was diluted with water
extractionThe reaction solution was subjected to extraction with ethyl acetate
washthe organic layer was washed with water
dry with materialdried over magnesium sulfate
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-672dd0019c9e43948578206fff7bef61
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586591B2

Reaction notes

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