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

HRID 418672Notes

Reaction equation

HRID 418672 reaction equation
[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

Participants

5

Reactant 2

HCID 59761,1-Dimethylhydrazine2×HCID 221435437-Chlorothieno[3,2-b]pyridine-2-carbonyl chloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-688e8c6d13144707b20963aff80b258a
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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