5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(3-methoxy-prop-1-ynyl)-nicotinamide → 5-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(3-methoxy-propyl)-nicotinamide

HRID 505963Notes

Reaction equation

HRID 505963 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:24]#[C:25][CH2:26][O:27][CH3:28])=[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>[Pd].C(OC(=O)C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([CH2:24][CH2:25][CH2:26][O:27][CH3:28])=[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 674260675-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(3-methoxy-prop-1-ynyl)-nicotinamide

Product 1

HCID 247974425-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(3-methoxy-propyl)-nicotinamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on charcoal (18 mg, 10%) was added to a solution of 5-(4-chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(3-methoxy-prop-1-ynyl)-nicotinamide (100 mg, 0.25 mmol) in ethylacetate (12 mL). The mixture was hydrogenated for 2 h at room temperature and 0.4 bar positive hydrogen pressure after which the theoretical amount of hydrogen had been consumed. The catalyst was then filtered off and the solvent was evaporated to afford 5-(4-Chloro-phenyl)-N-((1R,2R)-2-hydroxy-cyclohexyl)-6-(3-methoxy-propyl)-nicotinamide without further purification as a orange solid 93 mg (92% yield). m/z (ISP+): 403.2, 405.2 (M+H).

Workup

  1. custom0.4 bar positive hydrogen pressure after which the theoretical amount of hydrogen had been consumed
  2. filtrationThe catalyst was then filtered off
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e3f09fef395b4b1f88ac1c1acabdbe40
Source dataset
uspto-grants-2010_08
Patent number
US07781593B2

Reaction notes

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