Trifluoroacetic acid → 2-(6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-((cis)-3-fluoropiperidin-4-yloxy)quinoline

HRID 876442Notes

Reaction equation

HRID 876442 reaction equation
[F:1][C@H:2]1[C@@H:7]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[C:16]([C:19]2[N:23]4[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:22]4=[N:21][N:20]=2)[CH:15]=[CH:14]3)[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:28][C:25]1[CH:26]=[CH:27][C:22]2[N:23]([C:19]([C:16]3[CH:15]=[CH:14][C:13]4[C:18](=[C:9]([O:8][C@H:7]5[CH2:6][CH2:5][NH:4][CH2:3][C@H:2]5[F:1])[CH:10]=[CH:11][CH:12]=4)[N:17]=3)=[N:20][N:21]=2)[CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131731012HCID 131731012, compound

Product 1

HCID 672334812-(6-Fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-((cis)-3-fluoropiperidin-4-yloxy)quinolineYield 17.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(cis)-tert-butyl 3-fluoro-4-(2-(6-fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate (33 mg, 0.069 mmol) was dissolved in 2 mL DCM at ambient temperature. TFA (2 mL) was added and the mixture stirred at ambient temperature 1 hour. The reaction was evaporated under reduced pressure, and purified by preparative TLC eluting with 1:10 mixture of (0.5% NH4OH in MeOH):DCM to give the product (4.5 mg, 17% yield). MS APCI (+) m/z 382.1 (M+1) detected.

Workup

  1. customThe reaction was evaporated under reduced pressure
  2. custompurified by preparative TLC
  3. washeluting with 1:10 mixture of (0.5% NH4OH in MeOH)

Sources & evidence

ORD record
ord-fc19cc0d089e4c7797e95d491fe5a2fa
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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