Dimethylformamide → 4-[1-(2-chlorophenyl)-1H-indazol-3-yl]-1-piperazine carboxamide

HRID 359034

반응식

HRID 359034 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[N:9]1.[N+]([NH:26][C:27](N)=[O:28])([O-])=O.CN(C)C=O.C(OC(C)C)(C)C>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([N:17]2[CH2:22][CH2:21][N:20]([C:27]([NH2:26])=[O:28])[CH2:19][CH2:18]2)=[N:9]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7914Diisopropyl EtherHCID 62372NitroureaHCID 151170791-(2-chlorophenyl)-3-(1-piperazinyl)-1H-indazole

생성물 1

HCID 151171014-[1-(2-chlorophenyl)-1H-indazol-3-yl]-1-piperazine carboxamide수율 44.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 7.9 g of 1-(2-chlorophenyl)-3-(1-piperazinyl)-1H-indazole, 7.3 g of nitrourea and 100 ml of dimethylformamide was heated on a steam bath for 15 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated. The concentrate was flash chromatographed on silica gel eluting with chloroform/methanol (5%). Concentration of the appropriate fraction yielded a foam, which when stirred overnight with isopropyl ether afforded 4.0 g of 4-[1-(2-chlorophenyl)-1H-indazol-3-yl]-1-piperazine carboxamide as a powder. A 3.4 g sample of the free base was dissolved in diethyl ether and treated with 1.1 g of fumaric acid. The resulting salt was recrystallized from ethyl acetate to yield 2.3 g (22%) of 4-[1-(2-chlorophenyl)-1H-indazol-3-yl]-1-piperazine carboxamide hemifumarate, m.p. 156°-158°.

후처리

  1. temperaturewas heated on a steam bath for 15 minutes
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customchromatographed on silica gel eluting with chloroform/methanol (5%)
  7. customConcentration of the appropriate fraction yielded a foam, which when

출처 및 근거

ORD 기록
ord-de53b221082b433690531e16aba7a050
출처 데이터셋
uspto-grants-1991_03
특허 번호
US04999356

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