Phosphorus sulfide (P2S5) → HCID 86631245, compound

HRID 238660Notes

Reaction equation

HRID 238660 reaction equation
[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][N:20]([C:23](=O)[CH2:24][N:25]5[C:29]([CH3:30])=[CH:28][C:27]([C:31]([F:34])([F:33])[F:32])=[N:26]5)[CH2:19][CH2:18]4)[S:15][CH:16]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:37]>N1C=CC=CC=1>[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][N:20]([C:23](=[S:37])[CH2:24][N:25]5[C:29]([CH3:30])=[CH:28][C:27]([C:31]([F:34])([F:33])[F:32])=[N:26]5)[CH2:19][CH2:18]4)[S:15][CH:16]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 25256760HCID 25256760, compound2×

Product 1

HCID 86631245HCID 86631245, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-[4-[4,5-dihydro-5-phenyl-3-isoxazolyl]-2-thiazolyl]-1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]piperidine (i.e. the product of Example 1, Step B) (235 mg, 0.47 mmol) and phosphorus pentasulfide (104.5 mg, 0.235 mmol) in pyridine (5 ml) was heated under reflux for 2 h. The reaction mixture was then concentrated under reduced pressure, and the residue was distributed between dichloromethane (10 mL) and water (10 mL). The organic layer was washed with 1 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and brine, dried (MgSO4), and concentrated under reduced pressure to give 240 mg of the title product, a compound of the present invention, as a white foam.

Workup

  1. temperatureunder reflux for 2 h
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. washThe organic layer was washed with 1 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c9249c33dd14b358c7a61e88caea84a
Source dataset
uspto-grants-2014_02
Patent number
US08642634B2

Reaction notes

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