2-Aminopropanol → Rac-6-((3-butyl-5-methyl-isoxazol-4-yl)methoxy)-n-(2-hydroxy-1-methyl-ethyl)-nicotinamide

HRID 1807498Notes

Reaction equation

HRID 1807498 reaction equation
CO[C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([O: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][O: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 665991586-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

Product 1

HCID 49800448Rac-6-((3-butyl-5-methyl-isoxazol-4-yl)methoxy)-n-(2-hydroxy-1-methyl-ethyl)-nicotinamideYield 60%

Procedure

A mixture of 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (250 mg, 0.82 mmol), rac-2-amino-1-propanol (63 mg, 0.84 mmol) and TBD (29 mg, 0.21 mmol) was stirred for 15 h at room temperature under argon. The reaction mixture was concentrated onto silica then purified by chromatography (silica, 0 to 4% methanol in dichloromethane) to give the title compound (145 mg, 60%) as a white solid after trituration with diisopropyl ether. MS: m/e=348.3 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated onto silica
  2. customthen purified by chromatography (silica, 0 to 4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5a57e2973adc47b385b286f2d06922b9
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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