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

HRID 619673노트

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HRID 619673 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
5 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-b4cd12ff9d544f4ca403c2f054dabc49
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05959106

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