Trifluoroacetic acid → HCID 58734246, compound

HRID 2080502Notes

Reaction equation

HRID 2080502 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH:14]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([O:33][CH3:34])[CH:27]=2)(=[O:25])=[O:24])[C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])[C:11]([Cl:35])=[CH:10][N:9]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:35][C:11]1[C:12]([CH:14]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([O:33][CH3:34])[CH:27]=2)(=[O:25])=[O:24])[C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])=[CH:13][C:8]([NH2:7])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58734261HCID 58734261, compound

Product 1

HCID 58734246HCID 58734246, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a dichloromethane (5 ml) solution of t-butyl[5-chloro-4-[(4-chloro-3-methoxyphenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]carbamate (300 mg, 0.54 mmol) was added trifluoroacetic acid (5 ml) at 0° C. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue thus obtained was dissolved in dichloromethane. The resulting solution was washed with a 1N aqueous sodium hydroxide solution. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was washed with diethyl ether and then collected by filtration to give the title compound (208 mg, 0.45 mmol, 84%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue thus obtained
  3. washThe resulting solution was washed with a 1N aqueous sodium hydroxide solution
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue thus obtained
  8. washwas washed with diethyl ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c637163a814e49cd8639505ad8169e90
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

Loading…