Phosphorus oxychloride → HCID 68194586, compound

HRID 2370632Notes

Reaction equation

HRID 2370632 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:18](=[O:19])[C:17]2[C:12](=[N:13][C:14]([S:20][CH3:21])=[N:15][CH:16]=2)[NH:11][C:10]1=O.O=P(Cl)(Cl)[Cl:25].C(N(C(C)C)CC)(C)C>>[Cl:25][C:10]1[N:9]([C:3]2[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:18](=[O:19])[C:17]2[C:12]([N:11]=1)=[N:13][C:14]([S:20][CH3:21])=[N:15][CH:16]=2

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 68194993HCID 68194993, compound

Product 1

HCID 68194586HCID 68194586, compound

Procedure

A mixture of Example 95A (0.960 g, 2.83 mmol) in POCl3 (3.5 ml, 37.5 mmol) and diisopropylethylamine (DIEA) (3.5 ml, 20.04 mmol) was heated at 90° C. for 1.5 hours. After concentrating the reaction mixture, the residue was treated with ice and aqueous NaHCO3 solution and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, concentrated and purified on a 40 g silica column using the ISCO Companion flash system eluting with hexane/ethyl acetate (7:3 to 6:4) to provide the title compound.

Workup

  1. concentrationAfter concentrating the reaction mixture
  2. additionthe residue was treated with ice and aqueous NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on a 40 g silica column
  8. washeluting with hexane/ethyl acetate (7:3 to 6:4)

Sources & evidence

ORD record
ord-1339a36590b4474fb5c26cc305f9a561
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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