6-amino-12-methyl-8,9,11,12-tetrahydro-10H-[1,4]diazepino[1',2':1,2]imidazo[4,5-c]quinolin-10-one → 12-methyl-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1',2':1,2]imidazo[4,5-c]quinolin-6-amine
Reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]3[CH2:19][NH:18][C:17](=O)[CH2:16][CH:15]([CH3:21])[N:14]3[C:10]=2[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>C1COCC1>[CH3:21][CH:15]1[N:14]2[C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]([NH2:1])[C:11]=3[N:12]=[C:13]2[CH2:19][NH:18][CH2:17][CH2:16]1Participants
Procedure
Borane THF complex (2.76 mL of a 1 M solution in THF) was added to a solution of 6-amino-12-methyl-8,9,11,12-tetrahydro-10H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-10-one (0.389 g, 1.38 mmol) in THF (5 mL), and the mixture was stirred at room temperature overnight and then heated at reflux for six hours. An analysis by LC/MS indicated the reaction was incomplete, and additional borane tetrahydrofuran complex (2.76 mL) was added. The reaction mixture was heated at reflux overnight, allowed to cool, and concentrated under reduced pressure. The residue was treated with chloroform, and a solid was present that was isolated by filtration to provide 12-methyl-9,10,11,12-tetrahydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinolin-6-amine as a yellow solid.
Workup
- temperatureheated
- temperatureat reflux for six hours
- additionadditional borane tetrahydrofuran complex (2.76 mL) was added
- temperatureThe reaction mixture was heated
- temperatureat reflux overnight
- temperatureto cool
- concentrationconcentrated under reduced pressure
- additionThe residue was treated with chloroform
- customwas isolated by filtration
Sources & evidence
- ORD record
- ord-ed45a86b6c53450c82a8f811a3a4ec0a
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943609B2
Reaction notes
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