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Isopropylamine → 6-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid isopropylamide

HRID 1958069
ノート
印刷プレビュー

反応式

HRID 1958069 の反応式
C[Al](C)C.[CH:5]([NH2:8])([CH3:7])[CH3:6].C[O:10][C:11]([C:13]1[N:14]=[N:15][C:16]([O:19][CH2:20][C:21]2[C:22]([CH2:27][CH2:28][CH2:29][CH3:30])=[N:23][O:24][C:25]=2[CH3:26])=[CH:17][CH:18]=1)=O>C1(C)C=CC=CC=1.O1CCOCC1>[CH:5]([NH:8][C:11]([C:13]1[N:14]=[N:15][C:16]([O:19][CH2:20][C:21]2[C:22]([CH2:27][CH2:28][CH2:29][CH3:30])=[N:23][O:24][C:25]=2[CH3:26])=[CH:17][CH:18]=1)=[O:10])([CH3:7])[CH3:6]
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 666438716-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid methyl ester

生成物 1

HCID 666439296-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid isopropylamide収率 38%

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

Trimethylaluminium (0.72 mL of a 2 M solution in toluene, 1.44 mmol) was added dropwise to a stirred solution of isopropylamine (85 mg, 1.44 mmol) in dioxane (3 mL) at room temperature under argon. After 1 h, a solution of 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid methyl ester (110 mg, 0.36 mmol) in dioxane (3 mL) was added and the reaction mixture heated at 90° C. After 2 h the reaction mixture was cooled in an ice/water bath and quenched with Seignette salt solution (1 mL). The resultant mixture was filtered, the filter cake washed with dichloromethane, then the combined filtrates were concentrated then purified by chromatography (silica, 0 to 80% ethyl acetate in heptane) to give the title compound (45 mg, 38%) as a colourless oil. MS: m/e=333.4 [M+H]+.

後処理

  1. temperatureAfter 2 h the reaction mixture was cooled in an ice/water bath
  2. customquenched with Seignette salt solution (1 mL)
  3. filtrationThe resultant mixture was filtered
  4. washthe filter cake washed with dichloromethane
  5. concentrationthe combined filtrates were concentrated
  6. customthen purified by chromatography (silica, 0 to 80% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-fe949e606ecb4bb8a1293d99331bf34a
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08410104B2

反応ノート

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