Piracetam hydrazide → 1-({3-[3-(4-Fluorophenyl)-1H-Indazol-5-Yl]-1H-1,2,4-Triazol-5-Yl}Methyl)Pyrrolidine-2-One

HRID 1272981

반응식

HRID 1272981 반응식
Cl.C(O[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[NH:6])C.[NH2:23][NH:24][C:25](=O)[CH2:26][N:27]1[CH2:31][CH2:30][CH2:29][C:28]1=[O:32].C[O-].[Na+]>CO>[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([C:5]4[N:6]=[C:25]([CH2:26][N:27]5[CH2:31][CH2:30][CH2:29][C:28]5=[O:32])[NH:24][N:23]=4)[CH:8]=3)[NH:12][N:11]=2)=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 3565593Piracetam hydrazideHCID 10942334Sodium MethoxideHCID 22479739ethoxy[3-(4fluorophenyl)(1H-indazol-5-yl)]methanimine hydrochloride

생성물 1

HCID 224802561-({3-[3-(4-Fluorophenyl)-1H-Indazol-5-Yl]-1H-1,2,4-Triazol-5-Yl}Methyl)Pyrrolidine-2-One수율 34%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

A suspension of ethoxy[3-(4-fluorophenyl)(1H-indazol-5-yl)]methanimine hydrochloride (0.300 g, 0.94 mmol) and N-amino-2-(2-oxopyrrolidinyl)acetamide (0.442 g, 2.81 mmol) in 4 mL of anhydrous methanol was prepared. An excess of a commercial solution of sodium methoxide in methanol (0.643 mL, 4.37 M) was added. Upon adding the basic solution, the reaction mixture became clear then cloudy. After an hour, the temperature was raised to reflux temperature and was maintained for 48 hours. The reaction was then quenched with water, the pH adjusted to neutral and the crude product extracted with ethyl acetate. The title compound was purified by preparative HPLC (0.118 g, 34% yield): 1H NMR (CD3OD) δ 8.68 (s, 1H), 8.07–8.02 (m, 3H), 7.68 (d, 1H), 7.29 (t, 2H), 4.66 (s, 2H), 3.53 (t, 2H), 2.47 (t, 2H), 2.10 (quintet, 2H); ES-MS (m/z) 377 [M+H]+.

후처리

  1. customwas prepared
  2. additionUpon adding the basic solution
  3. waitAfter an hour
  4. temperaturethe temperature was raised
  5. temperatureto reflux temperature
  6. temperaturewas maintained for 48 hours
  7. customThe reaction was then quenched with water
  8. extractionextracted with ethyl acetate
  9. customThe title compound was purified by preparative HPLC (0.118 g, 34% yield)

출처 및 근거

ORD 기록
ord-d4c0a22030244ef0ad42d3921a6486bb
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208513B2

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