Trifluoroacetic acid → 5-(8-((trans)-3-Fluoropiperidin-4-yloxy)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-4-yl)oxazole

HRID 1095701Notes

Reaction equation

HRID 1095701 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]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[CH:27][C:22]4=[N:21][CH:20]=2)[CH:15]=[C:14]3[C:33]2[O:37][CH:36]=[N:35][CH:34]=2)[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: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]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[CH:27][C:22]4=[N:21][CH:20]=2)[CH:15]=[C:14]3[C:33]2[O:37][CH:36]=[N:35][CH:34]=2)[CH2:6][CH2:5][NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131729510(trans)-Tert-butyl 3-fluoro-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-4-(oxazol-5-yl)quinolin-8-yloxy)piperidine-1-carboxylate

Product 1

HCID 667821865-(8-((trans)-3-Fluoropiperidin-4-yloxy)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-4-yl)oxazoleYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (trans)-tert-butyl 3-fluoro-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-4-(oxazol-5-yl)quinolin-8-yloxy)piperidine-1-carboxylate (4 mg, 0.007 mmol) in DCM (1 mL) was added TFA (1 mL), followed by a 30 minute stir. The crude reaction was concentrated and purified by flash column chromatography (DCM/MeOH/NH4OH 10:1:0.1) affording the desired product (60%). MS APCI (+) m/z 504.2 (M+1) detected.

Workup

  1. customThe crude reaction
  2. concentrationwas concentrated
  3. custompurified by flash column chromatography (DCM/MeOH/NH4OH 10:1:0.1)

Sources & evidence

ORD record
ord-88a58a068e9e4949bc7bc4f3bdd715ef
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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