Dimethyl Sulfoxide → HCID 70085159, compound

HRID 1458752Notes

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) is heated at 110° C. overnight. The reaction mixture is cooled and then is poured into water. The mixture is extracted with CH2Cl2, and then the CH2Cl2 layer is evaporated. The residue is purified by column chromatography on silica gel eluting with 20% hexane/ethyl acetate to afford the product as the free base. The free base is then dissolved in methanol and is treated with methanesulfonic acid. The methanol is evaporated and the residue is 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 is cooled
extractionThe mixture is extracted with CH2Cl2
customthe CH2Cl2 layer is evaporated
customThe residue is purified by column chromatography on silica gel eluting with 20% hexane/ethyl acetate
customto afford the product as the free base
customThe methanol is evaporated
customthe residue is recrystallized from 2-propanol/ether
customdried in vacuo

Sources & evidence

ORD record: ord-8a8979a3749a4c629697518cab60e689
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05852035

Reaction notes

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