HCID 68551862, compound → HCID 57418369, compound

HRID 1868139Notes

Reaction equation

HRID 1868139 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:18]=[C:19]([C:23]4[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH:24]=4)[CH:20]=[CH:21][CH:22]=3)(=[O:16])=[O:15])[C@H:10]([CH3:36])[CH2:9]2)=[C:4]([C:37]([F:40])([F:39])[F:38])[CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([C:17]3[CH:18]=[C:19]([CH:23]4[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[CH2:25][CH2:24]4)[CH:20]=[CH:21][CH:22]=3)(=[O:15])=[O:16])[C@H:10]([CH3:36])[CH2:9]2)=[C:4]([C:37]([F:40])([F:38])[F:39])[CH:3]=1

Participants

4

Reactant 1

HCID 68551862HCID 68551862, compound

Product 1

HCID 57418369HCID 57418369, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 4-(3-(4-(4-fluoro-2-(trifluoromethyl)phenyl)-2-methylpiperazin-1-ylsulfonyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (620 mg, 1.06 mmol) in MeOH (50 mL) was added Pd/C (˜100 mg). The mixture was purged with nitrogen and then stirred under H2 balloon at room temperature for 2 h. The reaction mixture was filtered through Celite and concentrated. The crude product was purified by SiO2 gel column eluted with hexanes/EtOAc to give the titled compound as a light yellow solid (569 mg, 92%). HRMS: calcd for C28H35F4N3O4S+H+, 586.23572. found (ESI-FTMS, [M+H]1+), 586.23585.

Workup

  1. customThe mixture was purged with nitrogen
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated
  4. customThe crude product was purified by SiO2 gel column
  5. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-91877711fa004b6493d192fc7b56f7c2
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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