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Acetic Anhydride → n-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)acetamide

HRID 404871
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HRID 404871 반응식
[CH:1]([O:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[S:19][C:18]([CH:20]([N:22]4C(=O)C5[C:24](=CC=CC=5)[C:23]4=[O:32])[CH3:21])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].O.NN.C(N(CC)CC)C.C(OC(=O)C)(=O)C>ClCCl.CCCCCC.C(OCC)(=O)C.CO.C(O)C>[CH:1]([O:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[S:19][C:18]([CH:20]([NH:22][C:23](=[O:32])[CH3:24])[CH3:21])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]
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참가 물질

10

반응물 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 694391172-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)-1h-isoindole-1,3(2h)-dione

생성물 1

HCID 23648576n-(1-{5-[2-(4-Isopropoxyphenoxy)-1,3-thiazol-5-yl]thien-2-yl}ethyl)acetamide수율 24.2%

시약·촉매·용매 5

HCID 702Ethanol용매
HCID 887Methanol용매
HCID 6344Dichloromethane용매2회
HCID 8058Hexane용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of Example 3C (200 mg, 0.41 mmol) at room temperature in dichloromethane (5 mL) was added hydrazine hydrate (197 uL, 4.1 mmol). Ethanol was added until a clear, single phase was formed. After an hour at room temperature, the solvent was removed under vacuum and the reaction mixture was thoroughly dried. To the resulting mixture was added dichloromethane (5 mL), triethylamine (300 uL, 2.15 mmol) and acetic anhydride (150 uL, 1.59 mmol). After two hours at room temperature, methanol was added and the solution was stirred for additional hour. The mixture was concentrated and the product was isolated via silica column chromatography (using a gradient of 25 to 75% ethyl acetate in hexane) and yielded 40 mg of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.16-7.23 (m, 3H) 6.83-6.95 (m, 4H) 5.66 (d, J=8.09 Hz, 1H) 5.25-5.43 (m, 1H) 4.52 (heptet, J=6.25 Hz, 1H) 2.00 (s, 3H) 1.57 (d, J=6.99 3 H) 1.35 (d, J=6.25 Hz, 6H), MS (DCI): m/z 403 (M+H).

후처리

  1. customwas formed
  2. waitAfter an hour at room temperature
  3. customthe solvent was removed under vacuum
  4. customthe reaction mixture was thoroughly dried
  5. concentrationThe mixture was concentrated
  6. customthe product was isolated via silica column chromatography (

출처 및 근거

ORD 기록
ord-e4623637a0c54002b39fb3769ff31b34
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748627B2

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