tert-Butyl 3-(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)prop-2-ynylcarbamate → N-(1-Adamantylmethyl)-2-(3-aminopropyl)-5-chloroisonicotinamide hydrochloride

HRID 1247592Notes

Reaction equation

HRID 1247592 reaction equation
[C:1]12([CH2:11][NH:12][C:13]([C:15]3[C:20]([Cl:21])=[CH:19][N:18]=[C:17]([C:22]#[C:23][CH2:24][NH:25]C(=O)OC(C)(C)C)[CH:16]=3)=[O:14])[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]>[ClH:21].[C:1]12([CH2:11][NH:12][C:13](=[O:14])[C:15]3[C:20]([Cl:21])=[CH:19][N:18]=[C:17]([CH2:22][CH2:23][CH2:24][NH2:25])[CH:16]=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 21906674tert-Butyl 3-(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)prop-2-ynylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 21906695N-(1-Adamantylmethyl)-2-(3-aminopropyl)-5-chloroisonicotinamide hydrochlorideYield 117.7%

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

A stirred suspension of tert-butyl 3-(4-{[(1-adamantylmethyl)amino]carbonyl}-5-chloropyridin-2-yl)prop-2-ynylcarbamate (Example 6(i)) (0.34 g) and 5% rhodium on carbon was stirred under a positive pressure (2 barr) of hydrogen until no further uptake was observed. The mixture was filtered and concentrated. The residue was dissolved in a solution of hydrogen chloride in 1,4-dioxane (10 ml of a 4M solution) and left to stand for 0.5 hours. The solution was concentrated and the residue triturated with ethyl acetate to afford the titled compound (0.174 g) as a beige powder.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in a solution of hydrogen chloride in 1,4-dioxane (10 ml of a 4M solution) and
  4. waitleft
  5. concentrationThe solution was concentrated
  6. customthe residue triturated with ethyl acetate

Sources & evidence

ORD record
ord-e8dc9ff1d1a94f0095e4f4bdc63cc99d
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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