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

HRID 1923543
ノート
印刷プレビュー

反応式

HRID 1923543 の反応式
[CH:1]([NH2:4])([CH3:3])[CH3:2].C[Al](C)C.[CH2:9]([C:13]1[C:17]([CH2:18][CH2:19][C:20]2[S:21][C:22]([C:26](O)=[O:27])=[C:23]([CH3:25])[N:24]=2)=[C:16]([CH3:29])[O:15][N:14]=1)[CH2:10][CH2:11][CH3:12]>O1CCOCC1.C1(C)C=CC=CC=1>[CH:1]([NH:4][C:26]([C:22]1[S:21][C:20]([CH2:19][CH2:18][C:17]2[C:13]([CH2:9][CH2:10][CH2:11][CH3:12])=[N:14][O:15][C:16]=2[CH3:29])=[N:24][C:23]=1[CH3:25])=[O:27])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 666436692-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid

生成物 1

HCID 497820372-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid iso-propylamide収率 44.7%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒
HCID 31275
1,4-Dioxane
溶媒
2 回

反応条件

温度
90 °C

実験手順

To a stirred solution of isopropylamine (77 mg, 1.3 mmol) in dioxane (3 mL) under argon and at room temperature was added trimethylaluminium (0.65 mL of a 2M solution in toluene, 1.3 mmol). After 1 h, a solution of 2-[2-(3-butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid (100 mg, 0.32 mmol) in dioxane (4 mL) was added and the reaction mixture heated at 90° C. overnight. The reaction mixture was then 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 5% methanol in dichloromethane) gave the title compound (50 mg, 44%) as a light yellow oil. MS: m/e=350.5 [M+H]+.

後処理

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

出典と根拠

ORDレコード
ord-d44bd3e46c1b44eabe2876078a11c2f2
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08178522B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート