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

HRID 2283875

反応式

HRID 2283875 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c535de0b95184a009c37a744726012a8
出典データセット
uspto-grants-2015_09
特許番号
US09145410B2

関連ノート

読み込み中…