Propylene Glycol → N-(4-Chloro-2,6-difluorophenyl)-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide

HRID 619672Notes

Reaction equation

HRID 619672 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.C(O)C(O)C.Cl[S:17]([C:20]1[N:28]=[C:27]2[N:22]([C:23]([O:30][CH3:31])=[N:24][CH:25]=[C:26]2[F:29])[N:21]=1)(=[O:19])=[O:18]>ClCCl>[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH:6][S:17]([C:20]2[N:28]=[C:27]3[N:22]([C:23]([O:30][CH3:31])=[N:24][CH:25]=[C:26]3[F:29])[N:21]=2)(=[O:18])=[O:19])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 1030Propylene GlycolHCID 15125184-Chloro-2,6-DifluoroanilineHCID 109674702-Chlorosulfonyl-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine

Product 1

HCID 21846897N-(4-Chloro-2,6-difluorophenyl)-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 24.0 g (147 mmol) of 4-chloro-2,6-difluoroaniline and 22.9 g of 1,2-propanediol was placed in a round bottom flask and heated to 35° C. with stirring. A mixture of 14.5 g (49 mmol) of 88 percent purity 2-chlorosulfonyl-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine with 29.1 g of dichloromethane was prepared and was added in 1 mL shots over a 4 hour period. The resulting mixture was heated another 4 hours and was then stirred overnight at ambient temperature. It was then cooled to about 20° C. and filtered, collecting the solids present. The solids were slurried in 30 mL of a 1:1 mix of 2-propanol and water, collected by filtration, washed with 2×30 mL of 2-propanol, and air dried to obtain 14.8 g (75 percent of theory) of the title compound as a white powder of 98 percent purity melting at 203-204° C.

Workup

  1. customwas placed in a round bottom flask
  2. customwas prepared
  3. additionwas added in 1 mL shots over a 4 hour period
  4. temperatureThe resulting mixture was heated another 4 hours
  5. stirringwas then stirred overnight at ambient temperature
  6. temperatureIt was then cooled to about 20° C.
  7. filtrationfiltered
  8. customcollecting the solids present
  9. additionmix of 2-propanol and water
  10. filtrationcollected by filtration
  11. washwashed with 2×30 mL of 2-propanol, and air
  12. customdried

Sources & evidence

ORD record
ord-00dd6ca2cba44e86af6325928b852983
Source dataset
uspto-grants-1999_09
Patent number
US05959106

Reaction notes

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