Ethanolamine → 5-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide

HRID 1962949Notes

Reaction equation

HRID 1962949 reaction equation
C(O[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][O:17][C:18]=2[CH3:19])=[CH:8][N:7]=1)=[O:5])C.[CH2:26]([CH2:28][NH2:29])[OH:27].N12CCCNC1=NCCC2.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1>[OH:27][CH2:26][CH2:28][NH:29][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[C:15]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[N:16][O:17][C:18]=2[CH3:19])=[CH:8][N:7]=1)=[O:5]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 9357Potassium Sodium TartrateHCID 79873TriazabicyclodeceneHCID 666443955-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 498027535-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amideYield 88.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid ethyl ester (140 mg, 0.41 mmol) in toluene (1 mL) was added ethanolamine (30 mg, 0.49 mmol) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (35 mg, 0.25 mmol) and the reaction stirred under argon for 6 h. Seignette salt solution (4 mL) was added and the solution extracted with ethyl acetate (3×20 mL), dried, filtered, and concentrated in vacuo. Purification by chromatography (silica, 0 to 10% methanol in dichloromethane) afforded the title compound (128 mg, 88%) as a light yellow gum. MS: m/e=354.3 [M+H]+.

Workup

  1. extractionthe solution extracted with ethyl acetate (3×20 mL)
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography (silica, 0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-cfd421f25814425d9edc6311c8805ed3
Source dataset
uspto-grants-2013_04
Patent number
US08415379B2

Reaction notes

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