Water → HCID 136348012, compound

HRID 591748Notes

Reaction equation

HRID 591748 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]2[NH:23][C:22](=[O:24])[C:21]3[C:16](=[CH:17][C:18]([O:27][CH3:28])=[CH:19][C:20]=3[O:25][CH3:26])[N:15]=2)=[CH:9][C:8]=1[CH3:29].[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.O>CN(C=O)C>[CH3:29][C:8]1[CH:9]=[C:10]([C:14]2[NH:23][C:22](=[O:24])[C:21]3[C:16](=[CH:17][C:18]([O:27][CH3:28])=[CH:19][C:20]=3[O:25][CH3:26])[N:15]=2)[CH:11]=[C:12]([CH3:13])[C:7]=1[O:6][CH2:5][CH2:4][CH2:3][CH2:2][N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 136348011HCID 136348011, compound

Product 1

HCID 136348012HCID 136348012, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-(4-bromo-butoxy)-3,5-dimethyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one (494 mg, 1.07 mmol) in DMF (10 mL) was added pyrrolidine (609 mg, 8.57 mmol). The reaction mixture was stirred at room temperature for 16 hours. Water (100 mL) was added and the product was extracted with ethyl acetate (2×200 mL). The combined organic phase was washed with water, then brine, and dried over anhydrous Na2SO4. Solvent was evaporated to give the title compound as a white solid. Yield: 278 mg (57%). MP 180-181° C. 1H NMR (400 MHz, CDCl3): δ 7.68 (s, 2H), 6.83 (d, J=2.4 Hz, 1H), 6.46 (d, J=2.4 Hz, 1H), 3.97 (s, 3H), 3.92 (s, 3H), 3.83 (t, J=6.4 Hz, 2H), 2.56 (m, 6H), 2.36 (s, 6H), 1.88 (m, 2H), 1.79 (m, 6H). MS (ES) m/z: 452.21 (M+1).

Workup

  1. extractionthe product was extracted with ethyl acetate (2×200 mL)
  2. washThe combined organic phase was washed with water
  3. dry with materialbrine, and dried over anhydrous Na2SO4
  4. customSolvent was evaporated

Sources & evidence

ORD record
ord-3762b29051314a21b4029cfbef732a63
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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