Trifluoroacetic acid → HCID 58042380, compound

HRID 2048112Notes

Reaction equation

HRID 2048112 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:18][C:19]2[CH:31]=[CH:30][C:22]([C:23]([O:25]C(C)(C)C)=[O:24])=[CH:21][CH:20]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:18][C:19]2[CH:31]=[CH:30][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)[CH:5]=[N:6][C:7]=1[O:8][CH:9]([C:10]([F:12])([F:13])[F:11])[C:14]([F:16])([F:17])[F:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58042459HCID 58042459, compound

Product 1

HCID 58042380HCID 58042380, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (10 mL) solution of tert-butyl 4-(5-chloro-6-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)pyridin-3-ylamino)benzoate (Preparation 258, 220 mg, 0.47 mmol) was added trifluoroacetic acid (2 mL) at room temperature, and the reaction stirred for 18 hours. The reaction mixture was concentrated in vacuo and the residue was purified by reverse phase chromatography eluting with acetonitrile:water (5:95 to 95:5) to yield the title compound as a pale yellow solid (116 mg, 60%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by reverse phase chromatography
  3. washeluting with acetonitrile:water (5:95 to 95:5)

Sources & evidence

ORD record
ord-70710650d9a34266af6b4c6f6faf05f5
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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