Trifluoroacetic acid → HCID 66782087, compound

HRID 1095750Notes

Reaction equation

HRID 1095750 reaction equation
[F:1][C@H:2]1[C@@H:6]([O:7][C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[C:15]([C:18]2[N:22]4[CH:23]=[CH:24][C:25]([C:27]5[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=5)=[CH:26][C:21]4=[N:20][CH:19]=2)[CH:14]=[CH:13]3)[CH2:5][N:4](C(OCC2C=CC3C(=CC=CC=3)C=2)=O)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C@H:2]1[CH2:3][NH:4][CH2:5][C@H:6]1[O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([C:18]1[N:22]3[CH:23]=[CH:24][C:25]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[CH:26][C:21]3=[N:20][CH:19]=1)[CH:14]=[CH:13]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131729526HCID 131729526, compound

Product 1

HCID 66782087HCID 66782087, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of cis-naphthalen-2-ylmethyl 3-fluoro-4-(2-(7-(pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidine-1-carboxylate (2.0 mg, 0.003 mmol) in 1 ml DCM was cooled to 0° C. and 1 ml TFA was added. The mixture was stirred for 16 hours at ambient temperature and then concentrated. The residue was purified by preparative TLC, eluting with 15% MeOH/0.5% NE4OH in chloroform to give the title compound as a film (1.1 mg, 78% yield). MS APCI (+) m/z 426.2 (M+1) detected.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by preparative TLC
  3. washeluting with 15% MeOH/0.5% NE4OH in chloroform

Sources & evidence

ORD record
ord-ba676762f9904e9eb5b0ac8607f53633
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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