5-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(1-hydroxy-cyclopentylethynyl)-nicotinamide → 5-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-[2-(1-hydroxy-cyclopentyl)-ethyl]-nicotinamide

HRID 1929909Notes

Reaction equation

HRID 1929909 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:24]#[C:25][C:26]3([OH:31])[CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:10][CH:11]=[C:12]([CH:23]=2)[C:13]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[OH:22])=[O:14])=[CH:4][CH:3]=1>C(OC(=O)C)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([CH2:24][CH2:25][C:26]3([OH:31])[CH2:27][CH2:28][CH2:29][CH2:30]3)=[N:10][CH:11]=[C:12]([CH:23]=2)[C:13]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[OH:22])=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 675049925-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(1-hydroxy-cyclopentylethynyl)-nicotinamide

Product 1

HCID 675048385-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-[2-(1-hydroxy-cyclopentyl)-ethyl]-nicotinamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(1-hydroxy-cyclopentylethynyl)-nicotinamide (120 mg, 0.27 mmol) was dissolved in ethylacetate (15 mL) and hydrogenated in the presence of palladium on charcoal (10%) at room temperature and atmospheric pressure. After filtration and evaporation of the solvent the residue was purified by chromatography on silica gel with a ethyl acetate: methanol gradient to yield the product as colorless foam, MS (ISP) 443.1, 445.1 (M+H)+.

Workup

  1. filtrationAfter filtration and evaporation of the solvent the residue
  2. customwas purified by chromatography on silica gel with a ethyl acetate

Sources & evidence

ORD record
ord-846d75ee3d694315b7131d8ad9ed6d35
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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