Phosphorus oxychloride → HCID 59168618, compound

HRID 1444650Notes

Reaction equation

HRID 1444650 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][CH:12]([CH2:17][OH:18])[CH2:13][CH2:14][CH2:15][CH3:16])=O)[CH:5]=[CH:6][CH:7]=1.O=P(Cl)(Cl)Cl>>[CH2:13]([CH:12]1[CH2:17][O:18][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[N:11]1)[CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59168651HCID 59168651, compound

Product 1

HCID 59168618HCID 59168618, compound

Procedure

Compound 978 (50 mg) was treated with POCl3 (1.0 mL). This was stirred overnight. The solvent was removed via reduced pressure distillation. The residue was washd with aqueous sodium bicarbonate and then dissolved in EtOAc. The solvent was dried, filtered and evaporated. The residue was dissolved in acetone (1 mL) and refluxed with water (2 mL) for 1.5 hrs. The solution was extracted with EtOAc, the organic layer evaporated and the residue chromatographed on silica to give the target compound. 1H NMR (300 MHz, CDCl3) δ=7.38 (s, 1H), 7.15 (d, J=8.0 Hz, 1H), 7.05 (br, 1H), 7.00 (d, 7.5 Hz, 1H), 4.47 (m, 1H), 3.95 (m, 2H), 1.8-1.2 (m, 6H), 0.95 (m, 3H). ESIMS=224.9 m/z (M+H)

Workup

  1. customThe solvent was removed via reduced pressure distillation
  2. dissolutiondissolved in EtOAc
  3. customThe solvent was dried
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue was dissolved in acetone (1 mL)
  7. temperaturerefluxed with water (2 mL) for 1.5 hrs
  8. extractionThe solution was extracted with EtOAc
  9. customthe organic layer evaporated
  10. customthe residue chromatographed on silica
  11. customto give the target compound

Sources & evidence

ORD record
ord-e9798d075fa84db8ae9caaa796556b75
Source dataset
uspto-grants-2010_02
Patent number
US07662910B2

Reaction notes

Loading…