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

HRID 2368315ノート

反応式

HRID 2368315 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
2.5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d2738c320a7f4d5e8472ccf609599374
出典データセット
uspto-grants-2014_04
特許番号
US08703768B2

反応ノート

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