Dimethyl Sulfoxide → 1-ethyl-N-(adamantylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 1586146Notes

Reaction equation

HRID 1586146 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([CH2:15][CH3:16])[N:13]=[CH:14][C:3]=12.CS(C)=O.[C:21]12([CH2:31][NH2:32])[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[CH2:22]1)[CH2:28]2.CS(O)(=O)=O.CO>O>[CH2:15]([N:12]1[C:4]2=[N:5][C:6]3[C:11]([C:2]([NH:32][CH2:31][C:21]45[CH2:30][CH:25]6[CH2:24][CH:23]([CH2:29][CH:27]([CH2:26]6)[CH2:28]4)[CH2:22]5)=[C:3]2[CH:14]=[N:13]1)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH3:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 158169081-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinolineHCID 86749230Methanesulfonic acid methanol

Product 1

HCID 867492291-ethyl-N-(adamantylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amineYield 18.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]quinoline (1 g), DMSO (3 ml) and adamantylmethylamine (1 g) is heated at 110° C. overnight. The reaction mixture is poured into water, and a precipitate forms which is collected by filtration and dried to afford the product as a free base. The free base is treated with methanesulfonic acid/methanol, the methanol is evaporated and the salt is recrystallized from 2-propanol to afford 290 mg of 1-ethyl-N-(adamantylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine.CH3SO3H, m.p. 310° C.

Workup

  1. filtrationa precipitate forms which is collected by filtration
  2. customdried
  3. customto afford the product as a free base
  4. customthe methanol is evaporated
  5. customthe salt is recrystallized from 2-propanol

Sources & evidence

ORD record
ord-7e77c8deae934b3f8fc0cbd5a1eb4df4
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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