Acetic Acid → N-{2-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-1,3-thiazol-5-yl}acetamide

HRID 641511노트

반응식

HRID 641511 반응식
[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][C:17]4[S:18][C:19]([N+:22]([O-])=O)=[CH:20][N:21]=4)=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[C:30](O)(=[O:32])[CH3:31]>C(OC(=O)C)(=O)C.[Fe]>[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][C:17]4[S:18][C:19]([NH:22][C:30](=[O:32])[CH3:31])=[CH:20][N:21]=4)=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 103376233-Cyclobutyl-7-[(5-nitro-1,3-thiazol-2-yl)oxy]-2,3,4,5-tetrahydro-1H-3-benzazepine

생성물 1

HCID 10338403N-{2-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-1,3-thiazol-5-yl}acetamide

시약·촉매·용매 2

HCID 23925Iron촉매HCID 7918Acetic Anhydride용매

반응 조건

온도
80 °C

실험 절차

Iron powder (162 mg, 2.9 mmol) was added to a stirred solution of 3-cyclobutyl-7-[(5-nitro-1,3-thiazol-2-yl)oxy]-2,3,4,5-tetrahydro-1H-3-benzazepine (E210a) (162 mg, 0.47 mmol) in acetic acid (1 ml) and acetic anhydride (1 ml). The reaction mixture was stirred at 80° C. for 16 hours then cooled and poured onto ice. The solution was basified to pH 8 (sodium bicarbonate) and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried (sodium sulfate). Concentration in vacuo and subsequent purification of the resulting residue by column chromatography eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.3:2.7:97) afforded the title compound (E210). MS (ES+) m/e 358 [M+H]+.

후처리

  1. temperaturethen cooled
  2. additionpoured onto ice
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationConcentration
  7. customin vacuo and subsequent purification of the resulting residue by column chromatography
  8. washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.3:2.7:97)

출처 및 근거

ORD 기록
ord-68180582de384a22b6cca3feaa358551
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696193B2

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