Pyridine → N-methoxy-N-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxamide

HRID 1178764노트

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HRID 1178764 반응식
[N:1]1[N:2]2[CH2:11][CH2:10][CH2:9][C:3]2=[CH:4][C:5]=1[C:6]([O-])=[O:7].[K+].CN(C)C=O.C(Cl)(=O)C(Cl)=O.Cl.[CH3:25][NH:26][O:27][CH3:28].N1C=CC=CC=1>ClCCl.O>[CH3:28][O:27][N:26]([CH3:25])[C:6]([C:5]1[CH:4]=[C:3]2[CH2:9][CH2:10][CH2:11][N:2]2[N:1]=1)=[O:7]

참가 물질

8

반응물 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 58975587Potassium 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate

생성물 1

HCID 11356033N-methoxy-N-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxamide수율 89.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

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온도
5.5 °C

실험 절차

To a cooled (5-6° C.), stirred suspension of crude potassium 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate (0.82 g, 4.3 mmol) in dichloromethane (15 mL), containing N,N-dimethylformamide (0.1 mL, 1.3 mmol), is added, dropwise, oxalyl chloride (0.6 mL, 6.9 mmol). The reaction is exothermic with gas evolution. After the addition, the ice-bath is removed to allow the reaction mixture to stir at room temperature. After 3 hours, the solution is added to a stirred, cooled (10-12° C.) suspension of N,O-dimethylhydroxylamine hydrochloride (0.67 g, 6.9 mmol) in dichloromethane (7 mL) containing pyridine (1.7 mL, 21 mmol). After 40 minutes at room temperature, dichloromethane (35 mL) and water (25 mL) are added. The two layers are separated. The organic layer is extracted with water (2×25 mL), dried over anhydrous sodium sulfate, filtered and concentrated under diminished pressure to give 0.75 g (89% yield) of N-methoxy-N-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxamide as a brown solid.

후처리

  1. additionis added
  2. additionAfter the addition
  3. customthe ice-bath is removed
  4. stirringto stir at room temperature
  5. additionthe solution is added to a stirred
  6. temperaturecooled
  7. waitAfter 40 minutes at room temperature
  8. customThe two layers are separated
  9. extractionThe organic layer is extracted with water (2×25 mL)
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under diminished pressure

출처 및 근거

ORD 기록
ord-b463907f1b3f46de92c06a115f25fcbb
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276611B2

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