Ethanol → 6,7-dimethoxy-2-(1-m-tolyl-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl)-3H-quinazolin-4-one
Reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:15]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[N:9]=[CH:8]2)[CH:2]=1.Cl[C:18]1[NH:27][C:26](=[O:28])[C:25]2[C:20](=[CH:21][C:22]([O:31][CH3:32])=[C:23]([O:29][CH3:30])[CH:24]=2)[N:19]=1.C(N(CC)CC)C.C(O)C>COC(O)C>[CH3:30][O:29][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][C:22]=1[O:31][CH3:32])[N:19]=[C:18]([N:12]1[CH2:13][CH2:14][C:15]3[N:7]([C:3]4[CH:2]=[C:1]([CH3:16])[CH:6]=[CH:5][CH:4]=4)[CH:8]=[N:9][C:10]=3[CH2:11]1)[NH:27][C:26]2=[O:28]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 1-m-tolyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine 18a (100 mg, 0.5 mmol), 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one 1b (100 mg, 0.4 mmol), and triethylamine (140 μL, 1.0 mmol) in 10 mL methoxyethanol was heated at 100° C. under nitrogen for 12 hr. The mixture was pumped to constant weight. The resulting residue was slurried with hot ethanol and allowed to reach ambient temperature. Vacuum filtration provided 95 mg of 6,7-dimethoxy-2-(1-m-tolyl-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl)-3H-quinazolin-4-one, 601, [M+H]+=418, as a white solid.
Workup
- customto reach ambient temperature
- filtrationVacuum filtration
Sources & evidence
- ORD record
- ord-10b30f30a6b34483809b31f83eb5d43d
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900220B2
Reaction notes
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