Diisopropylamine → N-(2-Hydroxy-2-methylpropyl)-1-methyl-4-nitro-1H-pyrazole-3-carboxamide

HRID 467718노트

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HRID 467718 반응식
[CH3:1][N:2]1[CH:6]=[C:5]([N+:7]([O-:9])=[O:8])[C:4]([C:10]([OH:12])=O)=[N:3]1.[NH2:13][CH2:14][C:15]([CH3:18])([OH:17])[CH3:16].C(NC(C)C)(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C1COCC1.C(OCC)(=O)C>[OH:17][C:15]([CH3:18])([CH3:16])[CH2:14][NH:13][C:10]([C:4]1[C:5]([N+:7]([O-:9])=[O:8])=[CH:6][N:2]([CH3:1])[N:3]=1)=[O:12]

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 951022-Propanol, 1-amino-2-methyl-HCID 111923Propylphosphonic anhydrideHCID 5359761-Methyl-4-nitro-1H-pyrazole-3-carboxylic acid

생성물 1

HCID 70115746N-(2-Hydroxy-2-methylpropyl)-1-methyl-4-nitro-1H-pyrazole-3-carboxamide수율 31%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
2.5 °C

실험 절차

To a suspension of 1-methyl-4-nitro-1H-pyrazole-3-carboxylic acid (0.9 g, 5.26 mmol) and 1-amino-2-methylpropan-2-ol (469 mg, 5.26 mmol) in THF (20 mL) cooled to 0-5° C. were added N,N-diisopropylamine (3.67 mL, 21.0 mmol) and 1-propanephosphonic acid cyclic anhydride (8.37 mL, 13.1 mmol, 50% solution in ethyl acetate). The mixture was stirred at 70° C. for 16 hours, cooled to ambient temperature, poured into ethyl acetate (50 mL) and extracted with HCl (1 M, 20 mL). The organic phase was washed with water and brine. The aqueous layers were back-extracted separately with ethyl acetate and dichloromethane. The combined organic layers were dried and concentrated in vacuo to give 1.4 g crude product. The crude material was purified by silica gel chromatography using a methanol/ethyl acetate gradient to give the title compound as colorless foam (391 mg, 31% yield).

후처리

  1. temperaturecooled to ambient temperature
  2. extractionextracted with HCl (1 M, 20 mL)
  3. washThe organic phase was washed with water and brine
  4. extractionThe aqueous layers were back-extracted separately with ethyl acetate and dichloromethane
  5. customThe combined organic layers were dried
  6. concentrationconcentrated in vacuo
  7. customto give 1.4 g crude product
  8. customThe crude material was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-a5873c0601024180b817abf2468b720c
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623866B2

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