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

HRID 619673Notes

Reaction equation

HRID 619673 reaction equation
Cl[S:2]([C:5]1[N:13]=[C:12]2[N:7]([C:8]([O:15][CH3:16])=[N:9][CH:10]=[C:11]2[F:14])[N:6]=1)(=[O:4])=[O:3].C(O)C(O)C.[F:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25]>O>[F:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH:25][S:2]([C:5]1[N:13]=[C:12]2[N:7]([C:8]([O:15][CH3:16])=[N:9][CH:10]=[C:11]2[F:14])[N:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 1030Propylene GlycolHCID 95842-FluoroanilineHCID 109674702-Chlorosulfonyl-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine

Product 1

HCID 21846896N-(2-Fluorophenyl)-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 12.5 g (46.9 mmol) of 2-chlorosulfonyl-8-fluoro-5-methoxy[1,2,4]triazolo[1,5-c]pyrimidine and 25 mL of 1,2-propanediol was placed in a round bottom flask and cooled to 5° C. under nitrogen. 2-Fluoroaniline (13.7 g, 123 mmol) was added with stirring and cooling over a 10-min period. There was an exotherm. The mixture was allowed to warm to ambient temperature with stirring overnight and was then diluted with 30 mL of water. The mixture was stirred for 30 min and the solids present were then collected by filtration, washed with 2×25 mL of water and 2×25 mL of 2-propanol. The resulting solid was recrystallized from about 175 mL of 2-propanol and dried under reduced pressure at 45° C. to obtain 13.2 g (82.5 percent of theory) of the title compound as a white solid of 99 percent purity. The structure of this compound was confirmed by its proton nuclear magnetic resonance spectrum (300 MegaHertz, D-6 acetone): 9.70(s, 1H), 8.17(d, 1H, J=1.9 Hertz), 7.58(m, 1H), 7.24(m, 1H), 7.16(m, 2H), 4.29(s, 3H) and its C-13 carbon nuclear magnetic resonance spectrum (75 MegaHertz, D-6 acetone): 165.6, 156.8(d, J=244.8 Hertz), 149.1(d, J=26.1), 147.8, 145.7(d, J=252.9), 130.2(d, J=21.8), 128.5(d, J=4.1), 125(m), 116.7(d, J=19.7), 57.6.

Workup

  1. customwas placed in a round bottom flask
  2. temperaturecooling over a 10-min period
  3. temperatureto warm to ambient temperature
  4. stirringwith stirring overnight
  5. stirringThe mixture was stirred for 30 min
  6. filtrationthe solids present were then collected by filtration
  7. washwashed with 2×25 mL of water and 2×25 mL of 2-propanol
  8. customThe resulting solid was recrystallized from about 175 mL of 2-propanol
  9. customdried under reduced pressure at 45° C.

Sources & evidence

ORD record
ord-b4cd12ff9d544f4ca403c2f054dabc49
Source dataset
uspto-grants-1999_09
Patent number
US05959106

Reaction notes

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