Diisopropylethylamine → 2-Nitro-5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 449690노트

반응식

HRID 449690 반응식
Br[CH2:2][CH2:3][N:4]1[C:8]([CH2:9]Br)=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[N:5]1.[O:14]1[CH2:17][CH:16]([NH2:18])[CH2:15]1.C(N(C(C)C)CC)(C)C>C(#N)C>[N+:11]([C:6]1[CH:7]=[C:8]2[CH2:9][N:18]([CH:16]3[CH2:17][O:14][CH2:15]3)[CH2:2][CH2:3][N:4]2[N:5]=1)([O-:13])=[O:12]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 98339233-OxetanamineHCID 575020831-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole

생성물 1

HCID 667429562-Nitro-5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine수율 71.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 1-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole (500 mg, 1.6 mmol) in acetonitrile (20 mL) was added oxetan-3-amine (140 mg, 1.92 mmol) and diisopropylethyl amine (372 mg, 0.50 ml, 2.88 mmol) drop wise and the resulting mixture was stirred at room temperature for 24 h. The solution was concentrated and the residue dissolved in ethyl acetate (50 mL), washed with water (50 mL) and dried over magnesium sulfate. The resulting mixture was filtered and evaporated and the residue purified by flash chromatography (SF25-40 g, 50% to 100% ethyl acetate in hexanes) to give 2-nitro-5-oxetan-3-yl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazine (255 mg, 71%) as a light yellow solid.

후처리

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue dissolved in ethyl acetate (50 mL)
  3. washwashed with water (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe resulting mixture was filtered
  6. customevaporated
  7. customthe residue purified by flash chromatography (SF25-40 g, 50% to 100% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-715e76597b2e47b794e2df5ea17d2996
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481540B2

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