HCID 46872520, compound → HCID 59455878, compound

HRID 1942287Notes

Reaction equation

HRID 1942287 reaction equation
[CH2:1]([C:5]1[C:9](/[CH:10]=[CH:11]/[C:12]2[CH:24]=[CH:23][C:15]([C:16]([NH:18][CH:19]([CH3:22])[CH2:20][OH:21])=[O:17])=[CH:14][N:13]=2)=[C:8]([CH3:25])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4]>[Pd].C(O)C>[CH2:1]([C:5]1[C:9]([CH2:10][CH2:11][C:12]2[CH:24]=[CH:23][C:15]([C:16]([NH:18][CH:19]([CH3:22])[CH2:20][OH:21])=[O:17])=[CH:14][N:13]=2)=[C:8]([CH3:25])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 46872520HCID 46872520, compound

Product 1

HCID 59455878HCID 59455878, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred mixture of 6-[(E)-2-(3-butyl-5-methyl-isoxazol-4-yl)-vinyl]-N-(2-hydroxy-1-methyl-ethyl)-nicotinamide (example 10, 32 mg, 0.093 mmol) and 10% Palladium on charcoal (5 mg) in ethanol (5 mL) was shaken under an atmosphere of hydrogen for 2 h. The reaction mixture was filtered and concentrated. Purification by chromatography (silica, dichloromethane:methanol 100:0 to 9:1) afforded the title compound (20 mg, 63%) as a colorless oil. MS: m/e=364.4 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customPurification by chromatography (silica, dichloromethane:methanol 100:0 to 9:1)

Sources & evidence

ORD record
ord-664fb1fb31294eee82ed14f513b0d1c6
Source dataset
uspto-grants-2013_03
Patent number
US08389550B2

Reaction notes

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