Sodium hydride → 3-tert-butyl-4-chloro-N-(6-(2-chlorophenyl)-2-methoxy-3-nitropyridin-4-yl)-1-methyl-1H-pyrazole-5-carboxamide

HRID 570268

반응식

HRID 570268 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([O:14][CH3:15])[C:11]([N+:16]([O-:18])=[O:17])=[C:10]([NH2:19])[CH:9]=1.[H-].[Na+].[C:22]([C:26]1[C:27]([Cl:35])=[C:28]([C:32](O)=[O:33])[N:29]([CH3:31])[N:30]=1)([CH3:25])([CH3:24])[CH3:23].C(Cl)(=O)C(Cl)=O>C1COCC1.C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([O:14][CH3:15])[C:11]([N+:16]([O-:18])=[O:17])=[C:10]([NH:19][C:32]([C:28]2[N:29]([CH3:31])[N:30]=[C:26]([C:22]([CH3:24])([CH3:23])[CH3:25])[C:27]=2[Cl:35])=[O:33])[CH:9]=1

참가 물질

8

반응물 4

HCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 584254493-tert-butyl-4-chloro-1-methyl-1H-pyrazole-5-carboxylic acidHCID 674116886-(2-Chlorophenyl)-2-methoxy-3-nitropyridin-4-amine

생성물 1

HCID 674096383-tert-butyl-4-chloro-N-(6-(2-chlorophenyl)-2-methoxy-3-nitropyridin-4-yl)-1-methyl-1H-pyrazole-5-carboxamide

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 6-(2-chloro-phenyl)-2-methoxy-3-nitro-pyridin-4-ylamine (8.10 g, 29.0 mmol, prepared as described in the previous step) in THF (200 mL) was treated with NaH (3.47 g, 86.8 mmol, 60% dispersion in oil) at 0° C. for 1 h. Simultaneously a solution of 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid (6.90 g, 31.8 mmol, prepared as described in Example B) in DCM (200 mL) was treated with oxalyl chloride (3.2 mL, 36 mmol) and DMF (50 μL) at 0° C. and stirred at room temperature for 1 h. The volatile components were removed in vacuo, and the resulting residue was dried in vacuo for 15 min taken up in THF (20 mL) and added to the above sodium anilide solution at 0° C. The resulting mixture was stirred at room temperature for 30 min, quenched with saturated aqueous NH4Cl (20 mL), and extracted with EtOAc (3×100 mL). The combined extracts were dried over MgSO4 and concentrated in vacuo. The resulting solid was suspended in hexane (200 mL) and sonicated for 10 min and collected by suction filtration to yield 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [6-(2-chloro-phenyl)-2-methoxy-3-nitro-pyridin-4-yl]-amide as a tan-colored solid.

후처리

  1. customThe volatile components were removed in vacuo
  2. customthe resulting residue was dried in vacuo for 15 min
  3. additionadded to the above sodium anilide solution at 0° C
  4. stirringThe resulting mixture was stirred at room temperature for 30 min
  5. customquenched with saturated aqueous NH4Cl (20 mL)
  6. extractionextracted with EtOAc (3×100 mL)
  7. dry with materialThe combined extracts were dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customsonicated for 10 min
  10. filtrationcollected by suction filtration

출처 및 근거

ORD 기록
ord-c4190c57ad124421a463776f2107a50d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023846B2

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