Dimethyl Sulfoxide → 1-ethyl-N-[4-[2-(4-morpholinyl)ethoxy]phenylmethyl]-1H-pyrazolo[3,4-b]quinolin-4-amine

HRID 977142Notes

Reaction equation

HRID 977142 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].[N:17]1([CH2:23][CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][NH2:33])=[CH:28][CH:27]=2)[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.CS(C)=O>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:33][CH2:32][C:29]4[CH:28]=[CH:27][C:26]([O:25][CH2:24][CH2:23][N:17]5[CH2:22][CH2:21][O:20][CH2:19][CH2:18]5)=[CH:31][CH:30]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 7164631[4-(2-Morpholinoethoxy)phenyl]methylamineHCID 158169081-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline2×

Product 1

HCID 220975341-ethyl-N-[4-[2-(4-morpholinyl)ethoxy]phenylmethyl]-1H-pyrazolo[3,4-b]quinolin-4-amineYield 77.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (0.7 g, 3 mmol), 4-[2-(4-morpholinyl)ethoxy]phenylmethylamine (0.75 g, 3.2 mmol) and DMSO (3 mL) was heated on a steam bath for 8 hours. Additional 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (0.7 g, 3 mmol) was then added and the reaction mixture was heated on a steam bath for another 4 hours. The reaction mixture was cooled to room temperature and then was poured into water. The mixture was extracted with CH2Cl2 (3×100 mL) and then CH2Cl2 layers were combined, dried over MgSO4 and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with CH2Cl2 /methanol (95/5), followed by recrystallization from ethyl acetate, to afford 1.0 g of 1-ethyl-N-[4-[2-(4-morpholinyl) ethoxy]phenylmethyl]-1H-pyrazolo[3,4-b]quinolin-4-amine, as a yellow solid, m.p. 170°-172° C.

Workup

  1. temperaturewas heated on a steam bath for 8 hours
  2. temperaturethe reaction mixture was heated on a steam bath for another 4 hours
  3. extractionThe mixture was extracted with CH2Cl2 (3×100 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography on silica gel eluting with CH2Cl2 /methanol (95/5)
  7. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-51718b63e6cd4330b58a086308496109
Source dataset
uspto-grants-1997_03
Patent number
US05614530

Reaction notes

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