Piperidine → 7-bromo-2-(pyrrolidin-2-yl)quinazolin-4(3H)-one

HRID 1619345Notes

Reaction equation

HRID 1619345 reaction equation
C1C2C(COC([N:18]3[CH2:22][CH2:21][CH2:20][CH:19]3[C:23]3[NH:32][C:31](=[O:33])[C:30]4[C:25](=[CH:26][C:27]([Br:34])=[CH:28][CH:29]=4)[N:24]=3)=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CC#N.O>[Br:34][C:27]1[CH:26]=[C:25]2[C:30]([C:31](=[O:33])[NH:32][C:23]([CH:19]3[CH2:20][CH2:21][CH2:22][NH:18]3)=[N:24]2)=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 8082PiperidineHCID 136038175(9H-fluoren-9-yl)methyl 2-(7-bromo-4-oxo-3,4-dihydroquinazolin-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 1360381767-bromo-2-(pyrrolidin-2-yl)quinazolin-4(3H)-oneYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of (9H-fluoren-9-yl)methyl-2-(7-bromo-4-oxo-3,4-dihydroquinazolin-2-yl)pyrrolidine-1-carboxylate (305 mg, 1.04 mmol) and piperidine (2 mL) in CH3CN was stirred at room temperature for 2 h. The mixture was diluted with H2O (30 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give 162 mg of the desired product. MS (ESI): 294, 296 (MH+)

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-e4ebb1c2626e4c6994098f4a2646c673
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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