2-Aminopropanol → 6-[((3-Butyl-5-methyl-isoxazol-4-yl)methyl)-amino]-n-(2-hydroxy-1-methyl-ethyl)-nicotinamide

HRID 1807546Notes

Reaction equation

HRID 1807546 reaction equation
CO[C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[C:13]([CH2:18][CH2:19][CH2:20][CH3:21])=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.[NH2:23][CH:24]([CH3:27])[CH2:25][OH:26]>>[CH2:18]([C:13]1[C:12]([CH2:11][NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([NH:23][CH:24]([CH3:27])[CH2:25][OH:26])=[O:22])=[CH:5][N:6]=2)=[C:16]([CH3:17])[O:15][N:14]=1)[CH2:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 51262-AminopropanolHCID 66643788Methyl 6-(((3-butyl-5-methylisoxazol-4-yl)methyl)amino)nicotinate

Product 1

HCID 498016116-[((3-Butyl-5-methyl-isoxazol-4-yl)methyl)-amino]-n-(2-hydroxy-1-methyl-ethyl)-nicotinamideYield 54%

Conditions

Temperature
50 °C

Procedure

A mixture of 6-[(3-butyl-5-methyl-isoxazol-4-ylmethyl)-amino]-nicotinic acid methyl ester (90 mg, 0.3 mmol), rac-2-amino-1-propanol (27 mg, 0.36 mmol) and TBD (12 mg, 0.09 mmol) was heated at 50° C. for 4 h under argon. The reaction mixture was concentrated onto silica then purified by chromatography (silica, 0 to 7% methanol in ethyl acetate) to give the title compound (55 mg, 54%) as a colourless oil. MS: m/e=347.3 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated onto silica
  2. customthen purified by chromatography (silica, 0 to 7% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-77218a22455242319f4e885194a4756c
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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