Trifluoroacetic acid → HCID 86594361, compound

HRID 351370Notes

Reaction equation

HRID 351370 reaction equation
[CH:1]([NH:4][C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[CH2:16][CH2:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)=[CH:13][C:12]2=[O:27])[C@H:7]([CH2:28][S:29]([C:32]2[CH:37]=[CH:36][C:35](SC)=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH2:6]1)([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>CO.[Pd]>[CH:1]([NH:4][C@@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:24])[F:26])[CH:18]=3)[CH2:13][C:12]2=[O:27])[C@H:7]([CH2:28][S:29]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)(=[O:30])=[O:31])[CH2:6]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69035105HCID 69035105, compound

Product 1

HCID 86594361HCID 86594361, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of procedure (28e), (±) 1-[(1S*,2R*,4R*)-4-isopropylamino-2-(4-methylsulfanyl-benzenesulfonylmethyl)-cyclohexyl]-4-(3-trifluoromethyl-phenyl)-5,6-dihydro-1H-pyridin-2-one (˜10 mg), was dissolved in MeOH. The resulting solution was charged with ˜20 mg 10% Pd/C, stirred under 1 atm of H2 for 12 h, filtered, and concentrated in vacuo. The residue was redissolved in MeOH. The resulting solution was charged with ˜40 mg 10% Pd/C, stirred under 55 atm of H2 for 12 h, filtered, and concentrated in vacuo. The residue was redissolved in MeOH. The resulting solution was charged with ˜50 mg 10% Pd/C, stirred under 55 atm of H2 for 36 h, filtered, and concentrated in vacuo. The residue was dissolved in 0.5% TFA/MeCN and concentrated in vacuo to afford a mixture of diastereomers as the title compound as its TFA salt (10 mg). MS found: (M+H)+=537.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was redissolved in MeOH
  4. additionThe resulting solution was charged with ˜40 mg 10% Pd/C
  5. stirringstirred under 55 atm of H2 for 12 h
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was redissolved in MeOH
  9. additionThe resulting solution was charged with ˜50 mg 10% Pd/C
  10. stirringstirred under 55 atm of H2 for 36 h
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. dissolutionThe residue was dissolved in 0.5% TFA/MeCN
  14. concentrationconcentrated in vacuo
  15. customto afford

Sources & evidence

ORD record
ord-2118738a9c6947e7a93e36e3ec5b3174
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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