Water → HCID 22610940, compound

HRID 843565Notes

Reaction equation

HRID 843565 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:20])[C:5]([N:8]2[C:17](=[O:18])[CH:11]3[CH2:12][CH:13](O)[CH2:14][CH2:15][N:10]3[C:9]2=[O:19])=[N:6][CH:7]=1.C(N(S(F)(F)[F:27])CC)C.O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([F:20])[C:5]([N:8]2[C:17](=[O:18])[CH:11]3[CH2:12][CH:13]([F:27])[CH2:14][CH2:15][N:10]3[C:9]2=[O:19])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 22610939HCID 22610939, compound

Product 1

HCID 22610940HCID 22610940, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.6 g of 2-(5-chloro-3-fluoro-pyridin-2-yl)-7-hydroxitetrahydroimidazo-[1,5-a]-pyridin-1,3-dione (isomer B, Example H10) in 80 ml dichloromethane is treated at −55° C. to −65° C. with 1.9 ml of diethylaminosulfur trifluoride (DAST) and stirred at the same temperature for 1 hour. The reaction mixture is then allowed to stir at 20° C. over night. The resulting brownish solution is treated with ice and water and extracted with ethyl acetate. The combined extracts are washed with water, dried, filtered through a small silicagel column and evaporated to give the desired product with m.p. 154-157° C.

Workup

  1. stirringto stir at 20° C. over night
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts are washed with water
  4. customdried
  5. filtrationfiltered through a small silicagel column
  6. customevaporated

Sources & evidence

ORD record
ord-73f9cb8329b04e64b301f7b4770a85d9
Source dataset
uspto-grants-2002_04
Patent number
US06380134B1

Reaction notes

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