4-Amino-1-butanol → N-(4-Hydroxy-butyl)-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinamide

HRID 83336

Reaction equation

HRID 83336 reaction equation
CO[C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.[NH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30].N12CCCNC1=NCCC2.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[OH:30][CH2:29][CH2:28][CH2:27][CH2:26][NH:25][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 258684-Amino-1-butanolHCID 79873TriazabicyclodeceneHCID 516892Sodium BicarbonateHCID 665992926-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

Product 1

HCID 68441983N-(4-Hydroxy-butyl)-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinamideYield 37.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (180 mg, 0.55 mmol) and 4-amino-1-butanol (59 mg, 0.66 mmol) in toluene (1 mL) was added 1,5,7-triazabicyclo[4.4.0]dec-5-ene (23 mg, 0.17 mmol) and the reaction stirred under argon for 6 h at room temperature. Saturated aqueous sodium bicarbonate (1 mL) was then added and the resulting mixture was extracted with ethyl acetate (3×5 mL). The combined organic extracts were then dried over sodium sulfate and evaporated. Purification by chromatography (SiO2, dichloromethane:methanol=100:0 to 9:1) afforded the title compound (78 mg, 37%) which was obtained as a white solid. MS: m/e=382.2 [M+H]+.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (3×5 mL)
  2. dry with materialThe combined organic extracts were then dried over sodium sulfate
  3. customevaporated
  4. customPurification by chromatography (SiO2, dichloromethane:methanol=100:0 to 9:1)

Sources & evidence

ORD record
ord-47a99906c76f473eaed36e57c58f9355
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Linked notes

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