Pyridine → HCID 15789784, compound

HRID 1653966Notes

Reaction equation

HRID 1653966 reaction equation
[C:1]([O:4][CH:5]1[CH2:9][O:8][CH2:7][CH:6]1[O:10][C:11]([CH2:13][S:14][C:15]1[C:16]([Cl:31])=[CH:17][C:18]([F:30])=[C:19]([NH:21][C:22]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][NH:25]2)=[S:23])[CH:20]=1)=[O:12])(=[O:3])[CH3:2].N1C=CC=CC=1.[C:38](Cl)(Cl)=[O:39]>ClCCl.C1(C)C=CC=CC=1>[C:1]([O:4][CH:5]1[CH2:9][O:8][CH2:7][CH:6]1[O:10][C:11]([CH2:13][S:14][C:15]1[C:16]([Cl:31])=[CH:17][C:18]([F:30])=[C:19]([N:21]=[C:22]2[N:24]3[N:25]([CH2:26][CH2:27][CH2:28][CH2:29]3)[C:38](=[O:39])[S:23]2)[CH:20]=1)=[O:12])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 15789773HCID 15789773, compound

Product 1

HCID 15789784HCID 15789784, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

In 15 ml of dichloromethane was dissolved 1.48 g of 1-(5-(4-acetoxytetrahydrofuran-3-yloxycarbonylmethylthio)-4-chloro-2-fluorophenylaminothiocarbonyl)hexahydropyridazine, followed by addition of 0.59 g of pyridine, which was then cooled in an ice-cold bath. Under stirring, 3.3 g of a 26.8% solution of phosgene in toluene was added dropwise, and after addition was completed, the resulting product was stirred at room temperature for 3 hours. The reaction mixture was washed with water, subsequently with aqueous saturated sodium chloride solution, and dried over magnesium sulfate. After distilling off the solvent, the residue was purified by chromatography on a silica gel column (eluted with ethyl acetate/hexane=1/1), to obtain 1.20 g of a compound (No. 26) described in Table 1 (77%).

Workup

  1. temperaturewas then cooled in an ice-cold bath
  2. additionafter addition
  3. stirringthe resulting product was stirred at room temperature for 3 hours
  4. washThe reaction mixture was washed with water, subsequently with aqueous saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe residue was purified by chromatography on a silica gel column (eluted with ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-b9c965f49a644b94beebca841610f056
Source dataset
uspto-grants-1995_04
Patent number
US05405828

Reaction notes

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