Hydrochloric Acid → HCID 11488828, compound

HRID 2374281Notes

Reaction equation

HRID 2374281 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][C:8]=2[C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)[CH2:21][CH2:20]2)=[O:18])[CH2:3][CH2:2]1.Cl>CO.CCOCC>[CH3:16][S:13]([C:10]1[CH:11]=[CH:12][C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[C:8]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:29][CH:30]=3)[CH2:21][CH2:20]2)=[O:18])[CH:9]=1)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11375339HCID 11375339, compound

Product 1

HCID 11488828HCID 11488828, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of [2-(3,6-Dihydro-2H-pyran-4-yl)-5-methanesulfonyl-phenyl]-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, Example 60 (30 mg, 0.0607 mmol) in methanol (1.5 ml) was acidified to pH=1 with HCl solution in ether. The mixture was evaporated to dryness and the residue was taken up in Methanol (5 mL). Then Pd/C 10% (15 mg) was added and the mixture was hydrogenated at reflux temperature for 20 hours. The mixture was diluted with MeOH, filtered and the filtrate was concentrated in vacuo. The resulting mixture was purified on a SiO2: Eluent: Heptane/EtOAc 0% to 70% (20 minutes) then 70% (10 minutes) to provide the title compound (19 mg, white solid; Solid; M+H=497.2).

Workup

  1. customThe mixture was evaporated to dryness
  2. additionThen Pd/C 10% (15 mg) was added
  3. temperatureat reflux temperature for 20 hours
  4. additionThe mixture was diluted with MeOH
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resulting mixture was purified on a SiO2

Sources & evidence

ORD record
ord-ec3bc7af6ed347cc9e9c2ec03a616d35
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

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