Pyridine → HCID 18653361, compound

HRID 1653967Notes

Reaction equation

HRID 1653967 reaction equation
[C:1]([O:4][CH:5]1[CH2:9][O:8][CH2:7][CH:6]1[O:10][C:11]([CH2:13][O: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)=[S:39]>ClCCl>[C:1]([O:4][CH:5]1[CH2:9][O:8][CH2:7][CH:6]1[O:10][C:11]([CH2:13][O: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](=[S:39])[S:23]2)[CH:20]=1)=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10040ThiophosgeneHCID 54267155HCID 54267155, compound

Product 1

HCID 18653361HCID 18653361, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 15 ml of dichloromethane was dissolved 1.43 g of 1-(5-(4-acetoxytetrahydrofuran-3-yloxycarbonylmethoxy)-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, a solution of 0.52 g of thiophosgene in dichloromethane was added dropwise, and after addition was completed, the resulting mixture 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=2/3), to obtain 1.12 g of a compound (No. 42) described in Table 1 (72%).

Workup

  1. temperaturewas then cooled in an ice-cold bath
  2. additionafter addition
  3. stirringthe resulting mixture 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 the residue
  7. customwas purified by chromatography on a silica gel column (eluted with ethyl acetate/hexane=2/3)

Sources & evidence

ORD record
ord-f76ed55ab01c4287bb0d3b04a3c9897c
Source dataset
uspto-grants-1995_04
Patent number
US05405828

Reaction notes

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