Pyrrolidine → 2-[3-(Methyloxy)-4-nitrophenyl]-5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazole

HRID 419339노트

반응식

HRID 419339 반응식
Cl[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([O:17][CH3:18])[CH:9]=2)=[N:6][N:7]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCOCC1>[CH3:18][O:17][C:10]1[CH:9]=[C:8]([C:5]2[O:4][C:3]([CH2:2][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[N:7][N:6]=2)[CH:13]=[CH:12][C:11]=1[N+:14]([O-:16])=[O:15]

참가 물질

4

반응물 2

HCID 31268PyrrolidineHCID 594526612-(Chloromethyl)-5-[3-(methyloxy)-4-nitrophenyl]-1,3,4-oxadiazole

생성물 1

HCID 594529402-[3-(Methyloxy)-4-nitrophenyl]-5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazole수율 99%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To 2-(chloromethyl)-5-[3-(methyloxy)-4-nitrophenyl]-1,3,4-oxadiazole (Example 26, step C) (1.01 g, 3.75 mmol) in dioxane (10 mL) was added pyrrolidine (0.800 mL, 9.58 mmol). The reaction was stirred at rt overnight. Upon completion by TLC, the reaction mixture was treated with BOC-anhydride (0.371 g, 1.69 mmol) and cooled to 0° C. The mixture was treated with TEA (0.279 mL, 2.00 mmol). Purification by flash chromatography provided the title compound of step A (1.13 g, 3.70 mmol, 99%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.64-1.72 (m, 4H), 2.56 (br. s., 4H), 3.92-3.96 (m, 2H), 3.98-4.02 (m, 3H), 7.64-7.69 (m, 1H), 7.79 (br. s., 1H), 8.01-8.06 (m, 1H).

후처리

  1. temperaturecooled to 0° C
  2. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-5d323fd7674d46148f536f01b15bd23c
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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