Hydrochloric Acid → 1-ethyl-3-methyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 1456027Notes

Reaction equation

[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[C:5]([CH3:17])=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[NH4+].[OH-].Cl>C(Cl)Cl.O.CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:25][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[C:6]2[C:5]([CH3:17])=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-ethyl-3-methyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (1.0 g, 4.3 mmol), DMSO (3 ml) and benzylamine (0.98 ml, 9 mmol) was heated at 80° C. overnight. The reaction mixture was poured into water (100 ml), then NH4OH (0.5 ml) was added. The mixture was extracted with CH2Cl2 (200 ml) and the CH2Cl2 was concentrated to about 20 ml and then this solution was purified by column chromatography on silica gel, followed by high pressure liquid chromatography eluting with 20% ethyl acetate/hexane to afford the product as the free base. The free base was dissolved in CH2Cl2 (20 ml) and treated with ethereal HCl. The mixture was evaporated and the residue was crystallized from ether to afford 0.9 g of 1-ethyl-3-methyl-N-(phenylmethyl)-1H-pyrazolo[3,4-b]quinolin-4amine.HCl, as an off white solid, m.p. 228°-231° C.

Workup

extractionThe mixture was extracted with CH2Cl2 (200 ml)
concentrationthe CH2Cl2 was concentrated to about 20 ml
customthis solution was purified by column chromatography on silica gel
washeluting with 20% ethyl acetate/hexane
customto afford the product as the free base
customThe mixture was evaporated
customthe residue was crystallized from ether

Sources & evidence

ORD record: ord-d0130e50782548ba88229eb878adb914
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05843956

Reaction notes

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