Isopropylamine → 2-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid isoprop-ylamide

HRID 1923640노트

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HRID 1923640 반응식
[CH:1]([NH2:4])([CH3:3])[CH3:2].C[Al](C)C.C([O:11][C:12]([C:14]1[S:18][C:17]([O:19][CH2:20][C:21]2[C:22]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:23][O:24][C:25]=2[CH3:26])=[N:16][CH:15]=1)=O)C>O1CCOCC1.C1(C)C=CC=CC=1>[CH:1]([NH:4][C:12]([C:14]1[S:18][C:17]([O:19][CH2:20][C:21]2[C:22]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:23][O:24][C:25]=2[CH3:26])=[N:16][CH:15]=1)=[O:11])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 595684942-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid ethyl ester

생성물 1

HCID 497807072-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid isoprop-ylamide수율 69%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 312751,4-Dioxane용매2회

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온도
90 °C

실험 절차

To a stirred solution of isopropylamine (66 mg, 1.12 mmol) in dioxane (5 mL) under argon and at room temperature was added trimethylaluminium (0.60 mL of a 2M solution in toluene, 1.20 mmol). After 1 h, a solution of 2-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-thiazole-5-carboxylic acid ethyl ester (100 mg, 0.28 mmol) in dioxane (5 mL) was added and the reaction mixture warmed to 90° C. After 3 h, the reaction mixture was cooled, quenched with Seignettes's salt solution and water, then extracted with dichloromethane. The combined organic extracts were dried, filtered and concentrated. Purification by chromatography (silica, 0 to 3% methanol in dichloromethane) gave the title compound (68 mg, 69%) as a white solid. MS: m/e=358.1 [M+H]+.

후처리

  1. waitAfter 3 h
  2. temperaturethe reaction mixture was cooled
  3. customquenched with Seignettes's salt solution and water
  4. extractionextracted with dichloromethane
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (silica, 0 to 3% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-9153629c6cce432c999670414c42f5ca
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178522B2

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