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

HRID 1923640ノート

反応式

HRID 1923640 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
90 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-9153629c6cce432c999670414c42f5ca
出典データセット
uspto-grants-2012_05
特許番号
US08178522B2

反応ノート

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