HCID 59853753, compound → HCID 59853725, compound

HRID 2374280Notes

Reaction equation

HRID 2374280 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH:6][C:5]=1[C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:3])=[CH2:2]>C(OC(=O)C)C.C(Cl)Cl.[Pd]>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[O:11])=[O:12])=[CH:6][C:5]=1[C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:26][CH:27]=2)[CH2:18][CH2:17]1)=[O:15])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 59853753HCID 59853753, compound

Product 1

HCID 59853725HCID 59853725, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (2-Isopropenyl-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, (Example 44, 20 mg, 0.0442 mmol) in Ethylacetate (1 ml) was added Pd/C 10% (1 mg). The mixture was hydrogenated at rt for 1 hour. Then, Pd/C 10% (10 mg) and Ethylacetate (5mL) were added and the mixture was hydrogenated at reflux temperature for 1 hour. The mixture was diluted with MeCl2 ,filtered and the filtrate was concentrated in vacuo. The crude mixture was purified on SiO2 Eluent: Heptane/AcOEt 0% to 40% (20 minutes) to provide the title compound (14 mg, 70%, yellow solid); M+H=455.2

Workup

  1. temperatureat reflux temperature for 1 hour
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude mixture was purified on SiO2 Eluent

Sources & evidence

ORD record
ord-40ef3b4c03a14a4780d5756fe9a23c90
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

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