Dimethylformamide → N-(3-Chloropropyl)-3-({[(3-chloropropyl)amino]carbonyl}amino)-1H-pyrazole-1-carboxamide

HRID 32791

반응식

HRID 32791 반응식
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[Cl:7][CH2:8][CH2:9][CH2:10][N:11]=[C:12]=[O:13].[N-]=[C:15]=O.[CH2:17]([Cl:19])Cl.[CH3:20][N:21]([CH:23]=[O:24])C>>[Cl:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([N:4]1[CH:5]=[CH:6][C:2]([NH:1][C:23]([NH:21][CH2:20][CH2:15][CH2:17][Cl:19])=[O:24])=[N:3]1)=[O:13]

참가 물질

6

반응물 5

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 105034IsocyanateHCID 166752Propane, 1-chloro-3-isocyanato-HCID 178418806HCID 178418806, 화합물

생성물 1

HCID 59794354N-(3-Chloropropyl)-3-({[(3-chloropropyl)amino]carbonyl}amino)-1H-pyrazole-1-carboxamide수율 32%

실험 절차

To a solution of 3-aminopyrazole (500 mg, 6 mmol), in anh. DMF (10 mL), at r.t., under N2, was added 3-chloropropyl isocyanate (1.2 mL, 2 eq) and the reaction was stirred for 24 hr. The reaction was not complete and more isocyanate (1.2 mL, 2 eq) was added. The reaction mixture was stirred for an additional 48 hr. It was then poured into CH2Cl2/sat.aq. NaCl and the phases were separated. The aqueous layer was extracted with CH2Cl2 (2×20 mL) and the combined organic extracts were dried over anh. Na2SO4. The solids were filtered and the solvent evaporated. The crude product was purified by flash chromatography (Biotage 40, cHex/EtOAc 7:3) to give the title compound as a white solid (620 mg, 32%).

후처리

  1. stirringThe reaction mixture was stirred for an additional 48 hr
  2. customNaCl and the phases were separated
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×20 mL)
  4. dry with materialthe combined organic extracts were dried over anh. Na2SO4
  5. filtrationThe solids were filtered
  6. customthe solvent evaporated
  7. customThe crude product was purified by flash chromatography (Biotage 40, cHex/EtOAc 7:3)

출처 및 근거

ORD 기록
ord-056fb401bffd4356bf19d7e545d3779b
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427630B2

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