N-(1-Adamantylmethyl)-5-chloro-2-(3-hydroxy-1-propynyl)isonicotinamide → N-(1-Adamantylmethyl)-5-chloro-2-(3-hydroxypropyl)isonicotinamide

HRID 1247580Notes

Reaction equation

HRID 1247580 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=[O:25])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([C:21]#[C:22][CH2:23][OH:24])[CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H][H]>[Rh]>[C:1]12([CH2:11][NH:12][C:13](=[O:25])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([CH2:21][CH2:22][CH2:23][OH:24])[CH:15]=3)[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

4

Reactant 2

HCID 21906723N-(1-Adamantylmethyl)-5-chloro-2-(3-hydroxy-1-propynyl)isonicotinamideHCID 178418361HCID 178418361, compound

Product 1

HCID 21906688N-(1-Adamantylmethyl)-5-chloro-2-(3-hydroxypropyl)isonicotinamideYield 62.8%

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

A stirred suspension of N-(1-adamantylmethyl)-5-chloro-2-(3-hydroxy-1-propynyl)isonicotinamide (Example 1 (iii)) (0.48 g) and 5% rhodium on carbon (0.020 g) was stirred under a positive pressure (3 barr) of hydrogen until no further uptake was observed. The mixture was filtered and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate to afford the sub-titled compound (0.305 g) as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-e93cd577b26c4193acaf476d91274bf6
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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