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

HRID 524434Notes

Reaction equation

HRID 524434 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([O: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]([O: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 68182669Tert-butyl 6-[[2-(4-cyclopropylsulfonylphenyl)-2-(2,4-difluorophenoxy)acetyl]amino]pyridine-3-carboxylate

Product 1

HCID 687775406-[[2-(4-Cyclopropylsulfonylphenyl)-2-(2,4-difluorophenoxy)acetyl]amino]pyridine-3-carboxylic acidYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 6-[[2-(4-cyclopropylsulfonylphenyl)-2-(2,4-difluorophenoxy)acetyl]amino]pyridine-3-carboxylate (Example A7; 1.6 g, 2.94 mmole) in DCM (5 mL) was added TFA (7 mL) dropwise at 0° C. Reaction mixture was stirred at rt for 3 hr. TFA was removed invaccuo, residue was neutralised using sat.NaHCO3 solution, extracted with ethyl acetate (3×25 mL) washed with brine, dried over anhydrous sodium sulfate and concentrated. Crude solid was triturated in diisopropyl ether and filtered washed with diisopropyl ether to afford pure product (1.2 g).

Workup

  1. customReaction mixture
  2. customTFA was removed invaccuo, residue
  3. extractionNaHCO3 solution, extracted with ethyl acetate (3×25 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customCrude solid was triturated in diisopropyl ether
  8. filtrationfiltered
  9. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-3791cc7554324cfa85c70b6b5761fc3c
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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