Azetidine → Azetidin-1-yl(2-methyl-4-nitro-2H-pyrazol-3-yl)methanone

HRID 2368362

반응식

HRID 2368362 반응식
[CH3:1][N:2]1[C:6]([C:7]([OH:9])=O)=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=[N:3]1.[NH:13]1[CH2:16][CH2:15][CH2:14]1.C(N(C(C)C)CC)(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(OCC)(=O)C>[N:13]1([C:7]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][C:5]=2[N+:10]([O-:12])=[O:11])=[O:9])[CH2:16][CH2:15][CH2:14]1

참가 물질

6

반응물 4

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 5926231-Methyl-4-nitro-1H-pyrazole-5-carboxylic acid

생성물 1

HCID 70096944Azetidin-1-yl(2-methyl-4-nitro-2H-pyrazol-3-yl)methanone수율 73.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of 2-methyl-4-nitro-2H-pyrazole-3-carboxylic acid (300 mg, 1.75 mmol), azetidine (354 μl, 5.25 mmol) and diisopropylethylamine (920 μl, 5.26 mmol) in ethyl acetate (7.5 ml) was added 1-propanephosphonic acid cyclic anhydride (3.68 ml, 6.13 mmol; 50% in ethyl acetate) at 0° C. The ice bath was removed and stirring at r.t. was continued for 40 h. The reaction mixture was poured into ethyl acetate (100 ml) and extracted with sodium bicarbonate (saturated aqueous solution) water and brine. The aqueous layer was back-extracted with ethyl acetate, the combined organic phases were dried, evaporated, and the product was purified by silica gel chromatography using an amine phase and a heptane/ethyl acetate gradient to yield a white solid (269 mg, 73%).

후처리

  1. customThe ice bath was removed
  2. additionThe reaction mixture was poured into ethyl acetate (100 ml)
  3. extractionextracted with sodium bicarbonate (saturated aqueous solution) water and brine
  4. extractionThe aqueous layer was back-extracted with ethyl acetate
  5. customthe combined organic phases were dried
  6. customevaporated
  7. customthe product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-1e51b48315954a17ba5b8285fb84a243
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703768B2

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