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

HRID 1360552

Reaction equation

HRID 1360552 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-15cd89b947b54a6183fefc0ed5d0f756
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Linked notes

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