Phosphorus oxychloride → HCID 86711391, compound

HRID 926320Notes

Reaction equation

HRID 926320 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]1[C:16](=[O:17])[CH2:15][NH:14][C:13](=O)[CH:12]=[C:7]12.O=P(Cl)(Cl)Cl.[CH2:24]([C:26]1[N:27]=[CH:28][NH:29][CH:30]=1)[CH3:25]>ClCCCl>[CH2:24]([C:26]1[N:27]=[CH:28][N:29]([C:13]2[CH:12]=[C:7]3[C:8]4[C:3]([CH2:4][CH2:5][N:6]3[C:16](=[O:17])[CH2:15][N:14]=2)=[C:2]([I:1])[CH:11]=[CH:10][CH:9]=4)[CH:30]=1)[CH3:25]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 86711379HCID 86711379, compoundHCID 178437183HCID 178437183, compound

Product 1

HCID 86711391HCID 86711391, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

111-1. A mixture of 9-iodo-3,4,7,8-tetrahydro-[1,4]diazepino[7,1-a]isoquinoline-2,5-dione (440 mg, 1.24 mmol) in dry DCE (10 mL) was treated with POCl3 (0.23 mL, 2.49 mmol) and heated to 100° C. for 1 h. The mixture was allowed to cool to RT and then poured onto H2O and extracted with DCM. The combined org. layers were then dried over Na2SO4, filtered and concentrated in vacuo. The residue obtained was taken up in DCE (10 mL) and 4-ethyl-1H-imidazole (597 mg, 6.21 mmol) was added. The mixture was heated to 100° C. for 1 h. The mixture was then allowed to cool to RT, poured onto H2O, extracted with DCM and the combined org. layers were then dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (SiO2, DCM to DCM/MeOH 9:1) to give the title compound (523 mg) as a brown oil. UPLC-MS: MS 433.1 (M+H+); UPLC rt 0.93 min.

Workup

  1. temperatureto cool to RT
  2. additionpoured onto H2O
  3. extractionextracted with DCM
  4. dry with materiallayers were then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue obtained
  8. temperatureThe mixture was heated to 100° C. for 1 h
  9. temperatureto cool to RT
  10. additionpoured onto H2O
  11. extractionextracted with DCM
  12. dry with materiallayers were then dried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo
  15. customThe crude product was purified by flash chromatography (SiO2, DCM to DCM/MeOH 9:1)

Sources & evidence

ORD record
ord-2880682bdeea4d1596de938fb25bce21
Source dataset
uspto-grants-2016_03
Patent number
US09284331B2

Reaction notes

Loading…