Dimethyl Sulfoxide → HCID 67587896, compound

HRID 1458751Notes

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) is heated at 90° C. for 4 hours. The reaction mixture is poured into water, and the solid that forms is collected by filtration and recrystallized from ether/CH2Cl2/hexane to afford the product as the free base. The free base is dissolved in methanol (100 ml) and then is treated with methanesulfonic acid (1 ml). The methanol is evaporated, and then the residue is crystallized from 2-propanol/ether. The product is 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

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

Sources & evidence

ORD record: ord-4e502c79664a42c782093e1ff524360f
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05852035

Reaction notes

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