Trifluoroacetic acid → 6-(Piperazin-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 1674767Notes

Reaction equation

FC(F)(F)C(O)=O.[F:8][C:9]([F:33])([F:32])[C:10]1[N:14]2[CH:15]=[C:16]([N:19]3[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1>ClCCl>[N:19]1([C:16]2[CH:17]=[CH:18][C:13]3[N:14]([C:10]([C:9]([F:8])([F:33])[F:32])=[N:11][N:12]=3)[CH:15]=2)[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]1

Participants

Conditions

Temperature: 20 °C

Procedure

Trifluoroacetic acid (5 mL, 64.90 mmol) was added to a mixture of tert-butyl 4-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)piperazine-1-carboxylate (0.86 g, 2.32 mmol) and dichloromethane (20 mL). The resulting solution was stirred at 20° C. for 90 minutes and then evaporated to leave an involatile residue. The residue was purified by ion-exchange chromatography on an SCX column using aqueous ammonia (7M) in methanol as eluant to give 6-(piperazin-1-yl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine (0.540 g, 86%) as a yellow solid that was used without further purification.

Workup

customevaporated
customto leave an involatile residue
customThe residue was purified by ion-exchange chromatography on an SCX column

Sources & evidence

ORD record: ord-af033bef796a4506a68e430423e70a7d
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003649B2

Reaction notes

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