HCID 24753314, compound → HCID 24753222, compound

HRID 2356624Notes

Reaction equation

HRID 2356624 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[F:27])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([NH2:17])=O)[CH:12]=[CH:11][CH:10]=2)[CH:7]=1>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[F:27])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]#[N:17])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Participants

3

Reactant 1

HCID 24753314HCID 24753314, compound

Product 1

HCID 24753222HCID 24753222, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 6-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)-methyl]-2-pyridinecarboxamide (115 mg) in phosphoryl chloride (1.25 ml) was stirred at 60° C. for 5 hours. Excess phosphoryl chloride was removed in vacuo and ethyl acetate (5 ml) added. The solution was washed with saturated sodium bicarbonate solution (5 ml), and the aqueous layer extracted with ethyl acetate (5 ml). The combined extracts were washed with brine (5 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by mass-directed autopreparation to afford the title compound (93 mg, 85%) as a white solid.

Workup

  1. customExcess phosphoryl chloride was removed in vacuo and ethyl acetate (5 ml)
  2. additionadded
  3. washThe solution was washed with saturated sodium bicarbonate solution (5 ml)
  4. extractionthe aqueous layer extracted with ethyl acetate (5 ml)
  5. washThe combined extracts were washed with brine (5 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by mass-directed autopreparation

Sources & evidence

ORD record
ord-940cdf843d77425da87999e1cf7ce068
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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