Water → HCID 46912518, compound

HRID 591721Notes

Reaction equation

HRID 591721 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[N:22]([CH2:23][CH2:24][CH2:25]Br)[C:21](=[O:27])[C:20]3[C:15](=[CH:16][C:17]([O:30][CH3:31])=[CH:18][C:19]=3[O:28][CH3:29])[N:14]=2)=[CH:8][C:7]=1[CH3:32].[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1.O>CN(C=O)C>[CH3:32][C:7]1[CH:8]=[C:9]([C:13]2[N:22]([CH2:23][CH2:24][CH2:25][N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[C:21](=[O:27])[C:20]3[C:15](=[CH:16][C:17]([O:30][CH3:31])=[CH:18][C:19]=3[O:28][CH3:29])[N:14]=2)[CH:10]=[C:11]([CH3:12])[C:6]=1[O:5][CH2:4][CH2:3][CH2:2][N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 66675209HCID 66675209, compound

Product 1

HCID 46912518HCID 46912518, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-(3-bromo-propoxy)-3,5-dimethyl-phenyl]-3-(3-bromo-propyl)-5,7-dimethoxy-3H-quinazolin-4-one (0.76 g, 1.35 mmol) in DMF (10 mL) were added pyrrolidine (0.77 g, 10.77 mmol). The reaction mixture was stirred at room temperature for 16 hours. Then, water was added and product was extracted with ethyl acetate (2×200 mL). The combined organic layer was washed with water, then brine, and dried over Na2SO4. Solvent was evaporated to give the title compound as a white solid. Yield: 0.12 g (16%). MP 109-111° C. 1H NMR (400 MHz, CDCl3): δ 8.16 (s, 2H), 6.93 (d, J=2.4 Hz, 1H), 6.44 (d, J=2.4 Hz, 1H), 4.71 (t, J=6.4 Hz, 2H), 3.94 (s, 3H), 3.93 (s, 3H), 3.87 (t, J=6.0 Hz, 2H), 2.75 (m, 4H), 2.60 (m, 8H), 2.37 (s, 6H), 2.16 (m, 2H), 2.05 (m, 2H), 1.82 (m, 8H). MS (ES) m/z: 549.75 (M+1). Analysis calculated for C32H44N4O4.0.5H2O (FW 557.73), %: C, 68.91; H, 8.13; N, 10.05. Found, %: C, 68.71; H, 8.56; N, 9.74.

Workup

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

Sources & evidence

ORD record
ord-cdf5396e8fae4048a7840f94806805b7
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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