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

HRID 1958069
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인쇄 미리보기

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HRID 1958069 반응식
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]
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참가 물질

6

반응물 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 666438716-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid methyl ester

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매
HCID 31275
1,4-Dioxane
용매
2회

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온도
90 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-fe949e606ecb4bb8a1293d99331bf34a
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410104B2

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