4-Toluenesulfonyl chloride → HCID 86666437, compound

HRID 714413Notes

Reaction equation

HRID 714413 reaction equation
[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9]([C:11]2[C:12](=[O:30])[N:13]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][CH:16]=2)=[O:10])[CH:5]=[N:4]1)[CH3:2].C(N(CC)CC)C.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=1.[Cl-].[NH4+]>C(#N)C>[CH2:1]([N:3]1[C:7]([O:8][S:44]([C:41]2[CH:42]=[CH:43][C:38]([CH3:48])=[CH:39][CH:40]=2)(=[O:46])=[O:45])=[C:6]([C:9]([C:11]2[C:12](=[O:30])[N:13]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][CH:16]=2)=[O:10])[CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 178463137HCID 178463137, compound

Product 1

HCID 86666437HCID 86666437, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 5-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)carbonyl]-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone (i.e. the product from Example 3, Step B) (300 mg, 0.75 mmol) in acetonitrile (10 mL) was added triethylamine (116 mg, 1.12 mmol), followed by p-toluenesulfonyl chloride (171 mg, 0.90 mmol), and the reaction mixture was stirred at room temperature for 72 h. Saturated aqueous ammonium chloride solution was added to the mixture, and the aqueous layer was extracted with dichloromethane. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 50% ethyl acetate in hexanes to afford the title product, a compound of the present invention, as a white solid (160 mg).

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography
  5. washeluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f919e519ad7c4e6caa4694d1c99ef9d0
Source dataset
uspto-grants-2015_11
Patent number
US09187432B2

Reaction notes

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