Dimethyl Sulfoxide → HCID 70085159, compound

HRID 1456038Notes

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:28]=[CH:27][CH:26]=[CH:25][N:24]=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:28]=[CH:27][CH:26]=[CH:25][N:24]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (1.0 g, 0.0043 mol), DMSO (3 mL) and 2-aminomethylpyridine (0.9 mL, 0.0086 mol) was heated at 110° C. overnight. The reaction mixture was cooled and then was poured into water. The mixture was extracted with CH2 Cl2 and then the CH2Cl2 layer was evaporated. The residue was purified by column chromatography on silica gel eluting with 20% hexane/ethyl acetate to afford the product as the free base. The free base was then dissolved in methanol and was treated with methanesulfonic acid. The methanol was evaporated and the residue was recrystallized from 2-propanol/ether and dried in vacuo to afford 1.0 g of 1-ethyl-N-(2-pyridinylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine.2CH3SO3H, as a yellow solid m.p. 259°-260° C.

Workup

temperatureThe reaction mixture was cooled
extractionThe mixture was extracted with CH2 Cl2
customthe CH2Cl2 layer was evaporated
customThe residue was purified by column chromatography on silica gel eluting with 20% hexane/ethyl acetate
customto afford the product as the free base
customThe methanol was evaporated
customthe residue was recrystallized from 2-propanol/ether
customdried in vacuo

Sources & evidence

ORD record: ord-7227f177662645cca6a14d1bde1a7cf9
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05843956

Reaction notes

Loading…