Dimethylformamide → 4-chloro-2-phenyl-1-(2-piperidin-4-ylethyl)-2H-pyrazolo[3,4-c]quinoline

HRID 1095350Notes

Reaction equation

S(Cl)(Cl)=O.CN(C=O)C.[C:10]1([N:16]2[C:28]([CH2:29][CH2:30][CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)=[C:27]3[C:18]([C:19](=O)[NH:20][C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=43)=[N:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl:38]CCl>C(#N)C>[Cl:38][C:19]1[C:18]2=[N:17][N:16]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:28]([CH2:29][CH2:30][CH:31]3[CH2:32][CH2:33][NH:34][CH2:35][CH2:36]3)=[C:27]2[C:26]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Thionyl chloride (1.0 mL) and DMF (1.0 mL) were combined and added dropwise to a mixture of 2-phenyl-1-(2-piperidin-4-ylethyl)-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one (200 mg, 0.537 mmol) and dichloromethane (10 mL) at 0° C. The resulting suspension was stirred 5 minutes at 0° C. before warming to ambient temperature and stirring 55 minutes. The suspension was concentrated under reduced pressure to afford a light yellow oil that was stirred in acetonitrile and filtered to obtain a white solid. The solid was combined with additional acetonitrile and concentrated under reduced pressure to afford 100 mg of 4-chloro-2-phenyl-1-(2-piperidin-4-ylethyl)-2H-pyrazolo[3,4-c]quinoline.HCl as a white powder, mp 194° C. MS (APCI) m/z 391 (M+H)+; Anal. calcd for C23H23ClN4.1.0H2O.1.0HCl: C, 62.02; H, 5.88; N, 12.58. Found: C, 61.91; H, 5.67; N, 12.48.

Workup

temperaturebefore warming to ambient temperature
stirringstirring 55 minutes
concentrationThe suspension was concentrated under reduced pressure
customto afford a light yellow oil that
filtrationfiltered
customto obtain a white solid
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-4223314efc9d4b6a8a93755032442b2a
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138173B2

Reaction notes

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