Pyrrolidine → HCID 136348000, compound

HRID 591741Notes

Reaction equation

HRID 591741 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:20][C:19](=[O:21])[C:18]3[C:13](=[CH:14][C:15]([O:24][CH3:25])=[CH:16][C:17]=3[O:22][CH3:23])[N:12]=2)=[CH:7][CH:6]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C=O)C>[CH3:23][O:22][C:17]1[CH:16]=[C:15]([O:24][CH3:25])[CH:14]=[C:13]2[C:18]=1[C:19](=[O:21])[NH:20][C:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:6][CH:7]=1)=[N:12]2

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 136348013HCID 136348013, compound

Product 1

HCID 136348000HCID 136348000, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-[4-(2-bromo-ethoxy)-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one (0.25 g, 0.61 mmol) in anhydrous DMF (10 mL) was added pyrrolidine (0.20 mL, 2.45 mmol) and the reaction mixture was stirred at room temperature under nitrogen for about 20 hours. Solvent was removed under reduced pressure and the residual solid was triturated with water. The resulting slurry was filtered and washed with ether and hexanes. The crude product was purified by column chromatography (silica gel 230-400 mesh; 10% methanol in dichloromethane as eluent) to give the title compound as a white solid. Yield: 0.11 g (44%). MP 226-227° C. 1H NMR (400 MHz, CDCl3): δ 10.08 (br s, 1H), 8.07 (d, J=8.4 Hz, 2H), 7.06 (d, J=8.8 Hz, 2H), 6.81 (d, J=1.95 Hz, 1H), 6.45 (d, J=1.95 Hz, 1H), 4.21 (t, J=5.6 Hz, 2H), 3.99 (s, 3H), 3.93 (s, 3H), 2.97 (t, J=5.6 Hz, 2H), 2.68 (br s, 4H), 1.84 (br s, 4H). MS (ES+): m/z 198.65 (100%), 396.10 (M+1, 70%).

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residual solid was triturated with water
  3. filtrationThe resulting slurry was filtered
  4. washwashed with ether and hexanes
  5. customThe crude product was purified by column chromatography (silica gel 230-400 mesh; 10% methanol in dichloromethane as eluent)

Sources & evidence

ORD record
ord-f779101b023c4146bf85a6e8edc36865
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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