Furfurylamine → 1-ethyl-N-(2-furanylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine
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].[NH2:17][CH2:18][C:19]1[O:20][CH:21]=[CH:22][CH:23]=1>CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:17][CH2:18][C:19]4[O:20][CH:21]=[CH:22][CH:23]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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-aminomethylfuran (0.8 mL, 0.009 mol) was heated at 90° for 3 hours. The reaction mixture was then partitioned between CH2Cl2 (50 mL) and water (50 mL). The aqueous layer was separated and then extracted with CH2Cl2 (25 mL) and then the CH2Cl2 layers were combined, washed with water dried over Na2SO4 and reduced to a volume of about 3-5 mL. The solution was passed through a silica gel column eluting with ethyl acetate to afford the product which was recrystallized from ether/CH2Cl2 to afford 430 mg of 1-ethyl-N-(2-furanylmethyl)-1H-pyrazolo[3,4-b]quinolin-4-amine, as a yellow solid, m.p. 156-158° C.
Workup
- temperaturewas heated at 90° for 3 hours
- customThe reaction mixture was then partitioned between CH2Cl2 (50 mL) and water (50 mL)
- customThe aqueous layer was separated
- extractionextracted with CH2Cl2 (25 mL)
- washwashed with water
- dry with materialdried over Na2SO4
- washeluting with ethyl acetate
- customto afford the product which
- customwas recrystallized from ether/CH2Cl2
Sources & evidence
- ORD record
- ord-1ee94baab1424d48800392ad43904be8
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06008226
Reaction notes
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