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

HRID 359034
Notes
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Reaction equation

HRID 359034 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-de53b221082b433690531e16aba7a050
Source dataset
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04999356

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes