Dimethyl Sulfoxide → HCID 67587896, compound

HRID 1456037Notes

Reaction equation

[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].CS(C)=O.[NH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1.CS(O)(=O)=O>CO.O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:21][CH2:22][C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (1.0 g, 0.0043 mol), DMSO (1 mL) and 3-aminomethylpyridine (0.97 mL, 0.0093 mol) was heated at 90° C. for 4 hours. The reaction mixture was poured into water and the solid which formed was collected by filtration and recrystallized from ether/CH2Cl2 /hexane to afford the product as the free base. The free base was dissolved in methanol (100 mL) and then was treated with methanesulfonic acid (1 mL). The methanol was evaporated and then the residue was crystallized from 2-propanol/ether. The product was collected by filtration, washed with ether and dried in vacuo to afford 1.0 g of 1-ethyl-N-(3-pyridinylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine.2CH3SO3H, m.p. 282°-284° C.

Workup

customthe solid which formed
filtrationwas collected by filtration
customrecrystallized from ether/CH2Cl2 /hexane
customto afford the product as the free base
customThe methanol was evaporated
customthe residue was crystallized from 2-propanol/ether
filtrationThe product was collected by filtration
washwashed with ether
customdried in vacuo

Sources & evidence

ORD record: ord-cc10bcf051cb42cdab4d3c146fbc4486
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05843956

Reaction notes

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