Hydrochloric Acid → 1-(3-benzenesulfonylpropyl)-2-butyl-2H-pyrazolo[3,4-c]quinolin-4-amine

HRID 1984475

반응식

HRID 1984475 반응식
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10]([C:30]#[N:31])=[N:11][N:12]([CH2:26][CH2:27][CH2:28][CH3:29])[C:13]=1[CH2:14][CH2:15][CH2:16][S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:19])=[O:18]>C(O)C>[C:20]1([S:17]([CH2:16][CH2:15][CH2:14][C:13]2[N:12]([CH2:26][CH2:27][CH2:28][CH3:29])[N:11]=[C:10]3[C:9]=2[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[N:2]=[C:30]3[NH2:31])(=[O:19])=[O:18])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 669588264-(2-aminophenyl)-5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carbonitrile

생성물 1

HCID 577175051-(3-benzenesulfonylpropyl)-2-butyl-2H-pyrazolo[3,4-c]quinolin-4-amine수율 63.7%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

Hydrochloric acid (0.98 mL, 3.90 mmol) in ethanol was added dropwise to a solution of 4-(2-aminophenyl)-5-(3-benzenesulfonylpropyl)-1-butyl-1H-pyrazole-3-carbonitrile (550 mg, 1.30 mmol) in 10 mL of ethanol. The resultant solution was stirred for 2 hours, concentrated under reduced pressure, and diluted with water. The pH of the mixture was adjusted to 8-9 by slow addition of solid sodium carbonate. The aqueous layer was extracted with several portions of dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford a pale yellow solid. The material was purified via flash column chromatography on silica gel (eluting with a 97:3 mixture of dichloromethane/methanol) to afford 350 mg of 1-(3-benzenesulfonylpropyl)-2-butyl-2H-pyrazolo[3,4-c]quinolin-4-amine as a white crystalline solid, mp 206-207° C. 1H NMR (300 MHz, CDCl3) δ 7.87 (d, J=6.9 Hz, 2H), 7.77 (dd, J=1.2, 8.1 Hz, 1H), 7.69 (dd, J=0.9, 8.1 Hz, 1H), 7.63 (m, 1H), 7.53 (m, 2H), 5.37 (br s, 2H), 4.35 (app t, J=7.2 Hz, 2H), 3.45 (m, 2H), 3.22 (t, J=7.1 Hz, 2H), 2.23 (m, 2H), 1.94 (m, 2H), 1.40 (qd, J=7.2, 14.6 Hz, 2H), 0.98 (t. J=7.3 Hz, 3H); MS (APCI) m/z 423 (M+H+); Anal. calcd for C23H26N4O2S: C, 65.38; H, 6.20; N, 13.26. Found: C, 65.40; H, 6.01; N, 13.26.

후처리

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with water
  3. additionThe pH of the mixture was adjusted to 8-9 by slow addition of solid sodium carbonate
  4. extractionThe aqueous layer was extracted with several portions of dichloromethane
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford a pale yellow solid
  10. customThe material was purified via flash column chromatography on silica gel (
  11. washeluting with a 97:3 mixture of dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-a9a0bf3ba7934d068677b136d1ab9733
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544697B2

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