Pyrrolidine → HCID 22994356, compound

HRID 1167821Notes

Reaction equation

HRID 1167821 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:30])[O:10][C:11]3[C:16]([C:17]=2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27]Br)=[CH:21][CH:20]=2)=[CH:15][CH:14]=[C:13]([OH:29])[CH:12]=3)=[CH:4][CH:3]=1.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>C1COCC1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:30])[O:10][C:11]3[C:16]([C:17]=2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:21][CH:20]=2)=[CH:15][CH:14]=[C:13]([OH:29])[CH:12]=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 22994353HCID 22994353, compound

Product 1

HCID 22994356HCID 22994356, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(4-chlorophenyl)-4-(4-(2-bromoethoxy)benzyl)-7-hydroxychromen-2-one (8.3 g, 17.2 mmol) in 200 mL of THF was treated with 8 mL of pyrrolidine and the reaction mixture was heated at reflux for 5 h. The reaction mixture was concentrated and the crude product was purified using flash chromatography. The product was suspended in 250 mL of acetone and 4 mL of 5 M HCl(aq) was added. The mixture was stirred at room temperature overnight and the resulting solid was collected by filtration. The solid was suspended in 200 mL of ethyl acetate and the suspension was heated at reflux for 2h. The solution was cooled to room temperature and the final product was collected by filtration and dried under vacuum. The final yield was 4.96 grams (56%). 1H NMR (300 MHz, DMSO) δ 10.62 (s, 1H), 10.42 (s, 1H), 7.47 (d, 2H, J=8.5 Hz), 7.43 (d 1H, J=8.8 Hz), 7.34 (d, 2H, J=8.5 Hz), 7.09 (d, 2H, J=8.5 Hz), 6.87 (d, 2H, J=8.5 Hz), 6.77 (d, 1H, J=2.5 Hz), 6.71 (dd, 1H, J=2.5, 8.8 Hz), 4.26 (t, 2H, 4.9 Hz), 3.96 (s, 2H), 3.59-3.51 (m, 4H), 3.15-3.02 (m, 2H), 2.03-1.88 (m, 4H). MS (ESI) m/z 476 (M+H)+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 5 h
  3. concentrationThe reaction mixture was concentrated
  4. customthe crude product was purified
  5. addition4 mL of 5 M HCl(aq) was added
  6. filtrationthe resulting solid was collected by filtration
  7. temperaturethe suspension was heated
  8. temperatureat reflux for 2h
  9. temperatureThe solution was cooled to room temperature
  10. filtrationthe final product was collected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-0650123ae44d4a44bccac0eec7d73aa4
Source dataset
uspto-grants-2003_09
Patent number
US06620838B1

Reaction notes

Loading…