1-Phenethylamine → 3-(1-Phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-one
Reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:5]([N+:17]([O-])=O)=[CH:4][CH:3]=1.Cl[C:21]1[C:26]([N+]([O-])=O)=[CH:25][CH:24]=[C:23](Cl)[N:22]=1.C(N(C(C)C)CC)(C)C.[C:40]1(C(N)C)C=C[CH:43]=[CH:42][CH:41]=1.[O:49]1CCC[CH2:50]1>>[C:11]1([CH:9]([N:8]2[C:6]3=[N:7][C:2]([C:43]4[CH:42]=[CH:41][CH:40]=[C:21]5[C:26]=4[CH:25]=[CH:24][CH:23]=[N:22]5)=[CH:3][CH:4]=[C:5]3[NH:17][C:50]2=[O:49])[CH3:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
6
Conditions
- Temperature
- -78 °C
Procedure
6-Chloro-3-nitro-N-(1-phenylethyl)pyridin-2-amine. To a solution of 2,6-dichloro-3-nitropyridine (2.0 g, 10.4 mmol) in tetrahydrofuran (18 mL) at −78° C. was added diisopropylethylamine (2.17 mL, 12.4 mmol) and 1-phenylethanamine (1.51 g, 12.4 mmol). The reaction was maintained at −78° C. for 2 h and then allowed to slowly warm to room temperature overnight. Solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to afford the title compound (2.24 g, 78% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.68 (d, J=7.5, 1H), 8.42 (d, J=8.5, 1H), 7.45 (d, J=7.5, 2H), 7.34 (t, J=7.5, 2H), 7.25 (t, J=7.5, 1H), 6.80 (d, J=8.5, 1H), 5.36 (app quint, J=7, 1H), 1.57 (d, J=7, 3H).
Workup
- temperatureto slowly warm to room temperature overnight
- customSolvent was removed under reduced pressure
- customthe crude product was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-c55471e35e644277b9655063147e970e
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372976B2
Reaction notes
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