Trifluoroacetic acid → 8-(trans-3-Fluoropiperidin-4-yloxy)-2-(7-(pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)quinoline

HRID 1095747Notes

Reaction equation

HRID 1095747 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]=[CH:25][C:26]([C:28]5[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=5)=[CH:27][C:22]4=[N:21][CH: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.O>[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]=[CH:25][C:26]([C:28]5[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=5)=[CH:27][C:22]4=[N:21][CH:20]=2)[CH:15]=[CH:14]3)[CH2:6][CH2:5][NH:4][CH2:3]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66781535Tert-butyl trans-3-fluoro-4-(2-(7-(pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate

Product 1

HCID 667815808-(trans-3-Fluoropiperidin-4-yloxy)-2-(7-(pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)quinolineYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl trans-3-fluoro-4-(2-(7-(pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate (22 mg, 0.041 mmol) was added to 2 ml DCM at ambient temperature. TFA (2 mL) was added and the reaction was stirred for 1 hour, then diluted with DCM and water. The mixture was washed with 1N NaOH amine and extracted with DCM, followed by extraction with 20% IP A/Chloroform. The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by preparative TLC, eluting with 15% MeOH/0.5% NH4OH in DCM to provide the desired product as a film (5.6 mg, 31% yield). MS APCI (+) m/z 440.1 (M+1) detected.

Workup

  1. washThe mixture was washed with 1N NaOH amine
  2. extractionextracted with DCM
  3. extractionfollowed by extraction with 20% IP A/Chloroform
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC
  8. washeluting with 15% MeOH/0.5% NH4OH in DCM

Sources & evidence

ORD record
ord-d19d0b46e86044ca8ada5247f96c8f2d
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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