Trichloroacetonitrile → 3,5-diamino-N-[4-(4-methylpiperazin-1-yl)-3-pyridyl]-1H-pyrazole-4-carboxamide

HRID 524845노트

반응식

HRID 524845 반응식
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)=O)#[N:2].C([O-])(=O)C.[Na+].ClC(Cl)(Cl)[C:27]#[N:28].[OH2:31].[NH2:32][NH2:33]>C(O)C>[NH2:2][C:1]1[C:3]([C:4]([NH:6][C:7]2[CH:8]=[N:9][CH:10]=[CH:11][C:12]=2[N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[O:31])=[C:27]([NH2:28])[NH:33][N:32]=1

참가 물질

6

반응물 4

HCID 11011TrichloroacetonitrileHCID 24654Hydrazine hydrate (1:1)HCID 517045Sodium AcetateHCID 867209002-cyano-N-(4-(4-methylpiperazin-1-yl)pyridin-3-yl)acetamide

생성물 1

HCID 867208993,5-diamino-N-[4-(4-methylpiperazin-1-yl)-3-pyridyl]-1H-pyrazole-4-carboxamide수율 51.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a suspension of 2-cyano-N-[4-(4-methylpiperazin-1-yl)-3-pyridyl]acetamide 8 (1.6 g, 6.170 mmol) in ethanol (40 mL) was added sodium acetate (1.052 g, 12.83 mmol), followed by trichloroacetonitrile (1.042 g, 733.8 μL, 7.219 mmol) dropwise. The heterogeneous mixture was stirred at room temperature under an atmosphere of nitrogen for 18h. The reaction mixture was concentrated under vacuum, and the residue was dissolved in NMP (30 mL). Hydrazine hydrate (803 mg, 780.4 mL, 16.04 mmol) was added and the reaction mixture was stirred at room temperature for 3 h. The solvents were removed under vacuum and the residue triturated in DCM to form a brown solid which was isolated by filtration to provide 3,5-diamino-N-[4-(4-methylpiperazin-1-yl)-3-pyridyl]-1H-pyrazole-4-carboxamide 9 (1 g, 51%). MS (ES+) 317.1.

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved in NMP (30 mL)
  3. stirringthe reaction mixture was stirred at room temperature for 3 h
  4. customThe solvents were removed under vacuum
  5. customthe residue triturated in DCM
  6. customto form a brown solid which
  7. customwas isolated by filtration

출처 및 근거

ORD 기록
ord-0896618b17fb4f5a90a55c02185dbb72
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340546B2

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