Isopropylamine → 4-Methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid iso-propylamide

HRID 1923489ノート

反応式

HRID 1923489 の反応式
[CH:1]([NH2:4])([CH3:3])[CH3:2].C[Al](C)C.[CH3:9][C:10]1[N:11]=[C:12]([CH2:18][CH2:19][C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])[S:13][C:14]=1[C:15](O)=[O:16]>O1CCOCC1.C1(C)C=CC=CC=1>[CH:1]([NH:4][C:15]([C:14]1[S:13][C:12]([CH2:18][CH2:19][C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])=[N:11][C:10]=1[CH3:9])=[O:16])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 66643564HCID 66643564、化合物

生成物 1

HCID 497824864-Methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid iso-propylamide収率 54.1%

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 (216 mg, 3.65 mmol) in dioxane (4 mL) under argon and at room temperature was added trimethylaluminium (1.83 mL of a 2M solution in toluene, 3.7 mmol). After 1 h, a solution of 4-methyl-2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (300 mg, 0.91 mmol) in dioxane (4 mL) was added and the reaction mixture warmed to 90° C. After 4 h, the reaction mixture was cooled, quenched with ice water and extracted with dichloromethane. The combined extracts were washed with Seignette's salt solution then dried, filtered, and concentrated. Purification by chromatography (silica, 0 to 10% methanol in dichloromethane) gave the title compound (182 mg, 54%) as a light yellow gum. MS: m/e=370.1 [M+H]+.

後処理

  1. waitAfter 4 h
  2. temperaturethe reaction mixture was cooled
  3. customquenched with ice water
  4. extractionextracted with dichloromethane
  5. washThe combined extracts were washed with Seignette's salt solution
  6. customthen dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by chromatography (silica, 0 to 10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-bf483c2a34884c1c97c89b3607099cf5
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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