Trifluoroacetic acid → 6-[[2-(4-Cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino) acetyl]amino]pyridine-3-carboxylic acid

HRID 524435Notes

Reaction equation

HRID 524435 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=3[F:38])[C:14]([NH:16][C:17]3[N:22]=[CH:21][C:20]([C:23]([O:25]C(C)(C)C)=[O:24])=[CH:19][CH:18]=3)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([NH:30][C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=3[F:38])[C:14]([NH:16][C:17]3[N:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][CH:18]=3)=[O:15])=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68182771Tert-butyl 6-[[2-(4-cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetyl]amino]pyridine-3-carboxylate

Product 1

HCID 681824726-[[2-(4-Cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino) acetyl]amino]pyridine-3-carboxylic acidYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 6-[[2-(4-cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetyl]amino]pyridine-3-carboxylate (Example A8; 31 mg, 0.057 mmole) in DCM (1 mL) was added TFA at 0° C. Reaction mixture was stirred at rt for 1 hr. TFA was removed invaccuo, residue was neutralised using sat.NaHCO3 solution, extracted with ethyl acetate (3×10 mL) washed with brine, dried over anhydrous sodium sulfate and concentrated. Product was purified using preparative TLC, provided title compound (0.005 g).

Workup

  1. customReaction mixture
  2. customTFA was removed invaccuo, residue
  3. extractionNaHCO3 solution, extracted with ethyl acetate (3×10 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customProduct was purified

Sources & evidence

ORD record
ord-7420fde3a4654c6581eaa6d522b67ce8
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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