Phosphorus oxychloride → HCID 86651539, compound

HRID 1809456Notes

Reaction equation

HRID 1809456 reaction equation
O=P(Cl)(Cl)Cl.FC(F)(F)[C:8]([O-])=[O:9].C[NH2+]CC1C=CC(C2N=CC3N4C(NC(=O)CC=3)CCC=24)=CC=1.[C:36]([C:38]1[CH:43]=[CH:42][C:41]([C:44]2[N:45]=[C:46]3[CH:51]=[CH:50][CH:49]=[C:48]([C:52]([O:54][CH3:55])=[O:53])[N:47]3[CH:56]=2)=[CH:40][CH:39]=1)#[N:37]>CN(C=O)C>[C:36]([C:38]1[CH:43]=[CH:42][C:41]([C:44]2[N:45]=[C:46]3[CH:51]=[CH:50][CH:49]=[C:48]([C:52]([O:54][CH3:55])=[O:53])[N:47]3[C:56]=2[CH:8]=[O:9])=[CH:40][CH:39]=1)#[N:37]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 69810781HCID 69810781, compoundHCID 86651537HCID 86651537, compound

Product 1

HCID 86651539HCID 86651539, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

POCl3 (5.0 eq.) was added to a solution of Example 1, A2 in DMF (0.1 M) at RT. The reaction mixture was heated to reflux for 1 h. After cooling down, the reaction mixture was quenched by the addition of ice water, then, the aqueous phase was separated and extracted several times with DCM. The combined organic extracts were washed with brine and dried (Na2SO4). Evaporation of the solvent gave a residue which was purified by flash column on silica using a gradient of EtOAc/Petroleum ether from 40:60 to 70:30 to yield (58%) the title compound as a yellow powder. 1H NMR (400 MHz, DMSO-d6, 300K) δ 9.80 (1H, s), 8.22-8.15 (3H, m), 8.04 (2H, d, J=8.4 Hz), 7.87 (1H, dd, J=8.8, 7.0 Hz), 7.70 (1H, d, J=7.0 Hz), 3.92 (3H, s). MS (ES+) C17H11N3O3 requires: 305, found: 306 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. temperatureAfter cooling down
  4. customthe reaction mixture was quenched by the addition of ice water
  5. customthe aqueous phase was separated
  6. extractionextracted several times with DCM
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. customEvaporation of the solvent
  10. customgave a residue which
  11. customwas purified by flash column on silica using a gradient of EtOAc/Petroleum ether from 40:60 to 70:30

Sources & evidence

ORD record
ord-c0600b796af24a6bac3a04842a1d9f7c
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

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