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Sulfuric Acid → 2-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid isoprop-ylamide

HRID 1923637
Notes
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Reaction equation

HRID 1923637 reaction equation
CO[C:3]([C:5]1[S:9][C:8]([CH2:10][CH:11]([C:13]2[C:14]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:15][O:16][C:17]=2[CH3:18])O)=[N:7][CH:6]=1)=[O:4].S(=O)(=O)(O)O.[CH:28]([NH2:31])([CH3:30])[CH3:29]>>[CH:28]([NH:31][C:3]([C:5]1[S:9][C:8](/[CH:10]=[CH:11]/[C:13]2[C:14]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:15][O:16][C:17]=2[CH3:18])=[N:7][CH:6]=1)=[O:4])([CH3:30])[CH3:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 6363IsopropylamineHCID 666436782-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-2-hydroxy-ethyl]-thiazole-5-carboxylic acid methyl ester

Product 1

HCID 497815932-[(E)-2-(3-Butyl-5-methyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid isoprop-ylamideYield 34%

Conditions

Temperature
90 °C

Procedure

2-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-2-hydroxy-ethyl]-thiazole-5-carboxylic acid methyl ester (30 mg, 0.092 mmol) was stirred with concentrated sulfuric acid (0.1 mL) for 30 min, then the reaction mixture quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organic phases were dried, filtered and concentrated, then dissolved in toluene (0.5 mL) and isopropylamine (22 mg, 0.37 mmol) and TBD (13 mg, 0.092 mmol) added. The reaction mixture was then heated at 90° C. for 15 h and then the reaction mixture was concentrated then purified by chromatography (silica, 0 to 3% methanol in dichloromethane) to give the title compound (10 mg, 34%) as a pale yellow oil. MS: m/e=334.3 [M+H]+.

Workup

  1. customthe reaction mixture quenched with saturated sodium bicarbonate solution
  2. extractionextracted with ethyl acetate
  3. customThe combined organic phases were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutiondissolved in toluene (0.5 mL)
  7. concentrationthe reaction mixture was concentrated
  8. customthen purified by chromatography (silica, 0 to 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c6e19bc3750246d38f9967bd195ec022
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178522B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes