Methylamine → N-(1-Adamantylmethyl)-5-bromo-2-{[(2S)-2-hydroxy-3-(methylamino)propyl]oxy}isonicotinamide

HRID 1247613Notes

Reaction equation

HRID 1247613 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=[O:26])[C:14]3[C:19]([Br:20])=[CH:18][N:17]=[C:16]([O:21][CH2:22][C@@H:23]4[CH2:25][O:24]4)[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.[CH3:27][NH2:28]>O1CCOCC1>[C:1]12([CH2:11][NH:12][C:13](=[O:26])[C:14]3[C:19]([Br:20])=[CH:18][N:17]=[C:16]([O:21][CH2:22][C@@H:23]([OH:24])[CH2:25][NH:28][CH3:27])[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

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86595928N-(1-adamantylmethyl)-5-bromo-2-[(2S)-oxiran-2-ylmethoxy]isonicotinamide

Product 1

HCID 58721818N-(1-Adamantylmethyl)-5-bromo-2-{[(2S)-2-hydroxy-3-(methylamino)propyl]oxy}isonicotinamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-(1-adamantylmethyl)-5-bromo-2-[(2S)-oxiran-2-ylmethoxy]isonicotinamide (0.12 g) (Example 35(iii)), 40% aqueous methylamine (4 ml) and 1,4-dioxane (4 ml) was stirred for 4 hours. The reaction mixture was concentrated and the residue was purified by chromatography on silica gel eluting with ethyl acetate:ethanol:0.880 ammonia solution (4:1:0.1 to 1.5:1:0.1). The isolated material was dissolved in a solution of hydrogen chloride in 1,4-dioxane (10 ml of a 4M solution) and concentrated to afford the titled compound (0.039 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography on silica gel eluting with ethyl acetate
  3. dissolutionThe isolated material was dissolved in a solution of hydrogen chloride in 1,4-dioxane (10 ml of a 4M solution) and
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9829373b734f4852aa19614b686156bb
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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