HCID 59820074, compound → HCID 59820136, compound

HRID 2041096Notes

Reaction equation

HRID 2041096 reaction equation
[OH:1][C:2]1(/[CH:29]=[CH:30]/[C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)[CH2:7][CH2:6][N:5]([C:8](=[O:28])[CH2:9][O:10][CH2:11][CH2:12][N:13]([CH3:27])[S:14]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([O:24][CH3:25])=[CH:19][C:18]=2[CH3:26])(=[O:16])=[O:15])[CH2:4][CH2:3]1>CO.[Pd]>[OH:1][C:2]1([CH2:29][CH2:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)[CH2:3][CH2:4][N:5]([C:8](=[O:28])[CH2:9][O:10][CH2:11][CH2:12][N:13]([CH3:27])[S:14]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([O:24][CH3:25])=[CH:19][C:18]=2[CH3:26])(=[O:15])=[O:16])[CH2:6][CH2:7]1

Participants

4

Reactant 1

HCID 59820074HCID 59820074, compound

Product 1

HCID 59820136HCID 59820136, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (E)-N-(2-(2-(4-hydroxy-4-(2-(pyridin-3-yl)vinyl)piperidin-1-yl)-2-oxoethoxy)ethyl)-4-methoxy-N,2,6-trimethylphenylsulfonamide (0.9 mmol) in methanol (10 ml) was degassed for 15 min with argon, and 10% Pd/C (200 mg) was added. The resulting mixture was stirred for 16 h at 25° C. under a hydrogen atmosphere (conversion monitored by TLC). The reaction mixture was filtered through Celite, the filter cake was washed thoroughly with methanol, and the filtrate was concentrated completely. The residue was purified by column chromatography on silica gel (methylene chloride/methanol).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through Celite
  3. washthe filter cake was washed thoroughly with methanol
  4. concentrationthe filtrate was concentrated completely
  5. customThe residue was purified by column chromatography on silica gel (methylene chloride/methanol)

Sources & evidence

ORD record
ord-b35dd000ab3044feb492fa3d6e700e56
Source dataset
uspto-grants-2013_11
Patent number
US08580965B2

Reaction notes

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