Ethanolamine → HCID 49782713, compound

HRID 1923570Notes

Reaction equation

HRID 1923570 reaction equation
CO[C:3]([C:5]1[S:9][C:8](/[CH:10]=[CH: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:7][C:6]=1[CH3:24])=[O:4].[CH2:25]([CH2:27][NH2:28])[OH:26]>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[OH:26][CH2:25][CH2:27][NH:28][C:3]([C:5]1[S:9][C:8](/[CH:10]=[CH: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:7][C:6]=1[CH3:24])=[O:4]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 66643663HCID 66643663, compound

Product 1

HCID 49782713HCID 49782713, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 4-methyl-2-[(E)-2-(5-methyl-3-phenyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid methyl ester (70 mg, 0.21 mmol) in toluene (0.5 mL) was added ethanolamine (15 mg, 0.25 mmol) and TBD (18 mg, 0.13 mmol). After 24 h the reaction mixture was diluted with brine and extracted with ethyl acetate. The combined extracts were dried, filtered and concentrated in vacuo, then purified by chromatography (silica, 0 to 10% methanol in dichloromethane) to give the title compound (48 mg, 60%) as a pale yellow oil. MS: m/e=370.1 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe combined extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified by chromatography (silica, 0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-05702929580e4030b69f562a43ccbf0a
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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