Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH2:8].Cl[C:10]1[N:22]=[CH:21][CH:20]=[CH:19][C:11]=1[C:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:13].[H-].[Na+].O>O1CCOCC1>[CH2:17]([N:14]([CH2:15][CH3:16])[C:12](=[O:13])[C:11]1[CH:19]=[CH:20][CH:21]=[N:22][C:10]=1[NH:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[CH3:1])[CH3:18]Participants
Procedure
Into a 1-neck round-bottom flask was added 4-methylpyridin-3-amine (1.02 g, 0.00940 mol) and 2-chloro-N,N-diethylnicotinamide (2.00 g, 0.00940 mol) in 1,4-dioxane (20 mL), and then sodium hydride (0.94 g, 0.024 mol) was added. The reaction was heated at reflux for 1 hour. The mixture was allowed to cool and water was added. The mixture was then extracted with ethyl acetate 3× and the combined organic extracts were washed with water, brine, dried over MgSO4, and concentrate in vacuo. Upon cooling, the product crystallized. The crystalline solid was filtered off, washed with ether and dried to give 2.27 g of the desired product. 1H NMR (300 MHz, CDCl3): δ 9.15 (s, 1H), 8.21-8.24 (m, 2H), 7.90 (br s, 1H), 7.47 (dd, 1H J1=7.5, J2=1.8 Hz), 7.11 (d, 1H, J=4.8 Hz), 6.75 (dd, 1H, J1=7.5, J2=5.1 Hz), 3.46-3.51 (m, 4H), 2.29 (s, 3H), 1.25 (t, 6H). MS [M+1]=285.
Workup
- temperatureThe reaction was heated
- temperatureat reflux for 1 hour
- temperatureto cool
- extractionThe mixture was then extracted with ethyl acetate 3×
- washthe combined organic extracts were washed with water, brine
- dry with materialdried over MgSO4
- concentrationconcentrate in vacuo
- temperatureUpon cooling
- customthe product crystallized
- filtrationThe crystalline solid was filtered off
- washwashed with ether
- customdried
Sources & evidence
- ORD record
- ord-64ff0fe9c8d645dbbb29c3f35689905c
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835423B2
Linked notes
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