Trifluoroacetic acid → HCID 178461841, compound

HRID 1187693Notes

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-c049ad61c5704072a00a562611fa047c
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673891B2

Reaction notes

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