Trifluoroacetic acid → HCID 89704800, compound

HRID 929005Notes

Reaction equation

HRID 929005 reaction equation
[NH2:1][C:2]1[C:11]([S:12]CC2C=CC(OC)=CC=2)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])[C:3]=1[F:30].C(O)(C(F)(F)F)=O>C1(OC)C=CC=CC=1>[NH2:1][C:2]1[C:11]([SH:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])[C:3]=1[F:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89704787HCID 89704787, compound

Product 1

HCID 89704800HCID 89704800, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

To a solution of methyl 4-amino-3-fluoro-2-((2-fluorophenyl)amino)-5-((4-methoxybenzyl)thio)benzoate (9.79 g, 22.7 mmol) in anisole (12 mL) was added CF3COOH (20 mL). After stirring at ambient temperature for 23 h, the solvent was removed in vacuo. To the residue was added water (30 mL). The mixture was neutralized with 25% aqueous ammonia and extracted with ethyl acetate (100 mL×3). The combined organic layer was washed with water (100 mL×3) and brine (100 mL) sequentially, dried over Na2SO4, filtered and concentrated to give the desired product (white solid, 5.28 g, 75% yield). The product was used directly in the next step without further purification.

Workup

  1. customthe solvent was removed in vacuo
  2. additionTo the residue was added water (30 mL)
  3. extractionextracted with ethyl acetate (100 mL×3)
  4. washThe combined organic layer was washed with water (100 mL×3) and brine (100 mL) sequentially
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f9fd9e83c9ac4e76a3a81a91daf7b55a
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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