Dichloromethane → HCID 86609418, compound

HRID 1171654Notes

Reaction equation

HRID 1171654 reaction equation
[C:1]([S:4][CH:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])[CH2:7]/[C:6]/1=[CH:24]\[C:25]1[CH:29]=[CH:28][N:27]([CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])[N:26]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O.[Cl:45]CCl>>[ClH:45].[C:1]([S:4][CH:5]1[CH2:10][CH2:9][N:8]([CH:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[C:12]([CH:14]2[CH2:15][CH2:16]2)=[O:13])[CH2:7]/[C:6]/1=[CH:24]\[C:25]1[CH:29]=[CH:28][N:27]([CH2:30][C:31]([OH:33])=[O:32])[N:26]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86609420HCID 86609420, compound

Product 1

HCID 86609418HCID 86609418, compoundYield 80%

Procedure

To a solution of (E)-4-(acetylsulfanyl)-3-{[1-(t-butoxycarbonylmethyl)-1H-pyrazol-3-yl]methylidene}-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]piperidine (770 mg) in dichloromethane (10 ml) was added trifluoroacetic acid (10 ml) under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo, and the residue was diluted with ethyl acetate and washed saturated aqueous sodium hydrogencarbonate solution. The organic layer was neutralized with 1N hydrochloric acid and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, and the residue was dissolved in dichloromethane (10 ml) and a 4N solution of hydrogen chloride in dioxane (1.1 ml) was added to the resulting mixture. The reaction mixture was removed in vacuo, and the residue was purified by chromatography on a silica gel column using methanol and dichloromethane (1:40) as the eluent to afford the title compound (640 mg, yield: 80%) as a pale yellow amorphous solid.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed saturated aqueous sodium hydrogencarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. dissolutionthe residue was dissolved in dichloromethane (10 ml)
  8. additiona 4N solution of hydrogen chloride in dioxane (1.1 ml) was added to the resulting mixture
  9. customThe reaction mixture was removed in vacuo
  10. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-c852fa68197441d6a6cee573a14364bc
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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