Ethanolamine → HCID 46863230, compound

HRID 1942275Notes

Reaction equation

HRID 1942275 reaction equation
CO[C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7](/[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:6][CH:5]=1.[CH2:25]([CH2:27][NH2:28])[OH:26]>C1(C)C=CC=CC=1>[OH:26][CH2:25][CH2:27][NH:28][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7](/[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:6][CH:5]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 46872516HCID 46872516, compound

Product 1

HCID 46863230HCID 46863230, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
35 °C

Procedure

To a stirred solution of 6-[(E)-2-(5-methyl-3-phenyl-isoxazol-4-yl)-vinyl]-nicotinic acid methyl ester (200 mg, 0.62 mmol) in toluene (0.5 mL) was added ethanolamine (46 mg, 0.75 mmol) and TBD (26 mg, 0.10 mmol), then the reaction mixture was warmed to 35° C. After 3 h the reaction mixture was concentrated. Purification by chromatography (silica, dichloromethane:methanol 100:0 to 93:7) afforded the title compound (155 mg, 71%) as a white solid after trituration with hexane/ethyl acetate. MS: m/e=350.4 [M+H]+.

Workup

  1. concentrationAfter 3 h the reaction mixture was concentrated
  2. customPurification by chromatography (silica, dichloromethane:methanol 100:0 to 93:7)

Sources & evidence

ORD record
ord-a99a8fa7712d4cf4b8f2b3eb76e80b2a
Source dataset
uspto-grants-2013_03
Patent number
US08389550B2

Reaction notes

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