Ethanolamine → HCID 49793242, compound

HRID 1695333Notes

Reaction equation

HRID 1695333 reaction equation
CO[C:3]([C:5]1[NH:6][N:7]=[C:8]([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])[CH:9]=1)=[O:4].[CH2:24]([CH2:26][NH2:27])[OH:25].N12CCCNC1=NCCC2>C1(C)C=CC=CC=1>[OH:25][CH2:24][CH2:26][NH:27][C:3]([C:5]1[NH:6][N:7]=[C:8]([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])[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 79873TriazabicyclodeceneHCID 66643884HCID 66643884, compound

Product 1

HCID 49793242HCID 49793242, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester (100 mg, 0.32 mmol) and ethanolamine (29 mg, 0.47 mmol) in toluene (1 mL) was added 1,5,7-triazabicyclo[4.4.0]dec-5-ene (16 mg, 0.11 mmol) and the reaction was heated at 90° C. under argon overnight. After cooling to room temperature, the mixture was evaporated and purification by chromatography (silica, dichloromethane:methanol=100:0 to 9:1) afforded the title compound (30 mg, 28%), which was obtained as a white solid. MS: m/e=343.2 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was evaporated
  3. custompurification by chromatography (silica, dichloromethane:methanol=100:0 to 9:1)

Sources & evidence

ORD record
ord-6fc96975a5f045a78ec6caaa06dc3d3a
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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