1,1-Dimethylhydrazine → 7-chloro-N',N'-dimethylthieno[3,2-b]pyridine-2-carbohydrazide

HRID 418672노트

반응식

HRID 418672 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11](Cl)=[O:12])[S:10][C:3]=12.[CH3:14][N:15]([CH3:17])[NH2:16]>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([NH:16][N:15]([CH3:17])[CH3:14])=[O:12])[S:10][C:3]=12

참가 물질

5

반응물 2

HCID 59761,1-Dimethylhydrazine2회HCID 221435437-Chlorothieno[3,2-b]pyridine-2-carbonyl chloride

생성물 1

HCID 587901507-chloro-N',N'-dimethylthieno[3,2-b]pyridine-2-carbohydrazide수율 72.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of 7-chlorothieno[3,2-b]pyridine-2-carbonyl chloride 20 (1 g, 4.33 mmol) (scheme 6) in DCM (22 mL), 1,1-dimethylhydrazine (0.33 mL, 4.33 mmol) was added in one portion and the mixture was stirred for 5 h. More 1,1-dimethylhydrazine (0.33 mL, 4.33 mmol) was added and the mixture was stirred overnight at room temperature. The crude was diluted with EtOAc, extracted with 1N HCl, the aqueous solution basified to pH˜11 by addition of 1N NaOH, extracted with EtOAc, the organic phase dried over anhydrous Na2SO4 and concentrated under reduced pressure affording 237 (798 mg, 3.13 mmol, 72%) as a crude mixture that was used in the next step without further purification. MS (m/z): (M+1) 255.9 (100%), 257.9 (39%).

후처리

  1. additionwas added in one portion
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionextracted with 1N HCl
  4. additionthe aqueous solution basified to pH˜11 by addition of 1N NaOH
  5. extractionextracted with EtOAc
  6. dry with materialthe organic phase dried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-688e8c6d13144707b20963aff80b258a
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093264B2

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