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

HRID 1349834

Reaction equation

HRID 1349834 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-b09a52db5b314b319dd4f21770f7d0f3
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Linked notes

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