Pyridine → HCID 22049782, compound

HRID 1830871Notes

Reaction equation

HRID 1830871 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=2)[N:13]=1.N1C=CC=CC=1.[C:29](Cl)(=[O:31])[CH3:30]>ClCCl>[F:22][C:2]([F:21])([F:1])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]1[S:10][CH:11]=[C:12]([C:14]2[CH:20]=[CH:19][C:17]([NH:18][C:29](=[O:31])[CH3:30])=[CH:16][CH:15]=2)[N:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 22049719HCID 22049719, compound

Product 1

HCID 22049782HCID 22049782, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound (156) (0.20 g, 0.63 mmol) in dichloromethane (3 ml) were added pyridine (0.05 ml, 0.63 mmol) and acetyl chloride (0.04 ml, 0.63 mmol) under ice-cooling. The reaction mixture was warmed to room temperature and, after stirring for one hr., partitioned between ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate, and the extracts were combined and dried (MgSO4). The solvent was evaporated under reduced pressure. The obtained residue was crystallized from ethyl acetate to give white crystals (0.17 g, 76%).

Workup

  1. temperaturecooling
  2. custom, partitioned between ethyl acetate and brine
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-5c7698e2476c49bf9d827d3b0cbaed73
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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