Dimethylamine → 6-dimethylamino-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridine-2-amine
Reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[N:10]=[C:9]([N:11]([CH2:14][C:15]2[S:19][C:18]([Cl:20])=[N:17][CH:16]=2)[CH2:12][CH3:13])[C:8]([N+:21]([O-:23])=[O:22])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][N:2]([CH3:3])[C:5]1[N:10]=[C:9]([N:11]([CH2:14][C:15]2[S:19][C:18]([Cl:20])=[N:17][CH:16]=2)[CH2:12][CH3:13])[C:8]([N+:21]([O-:23])=[O:22])=[CH:7][CH:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
1.15 g of 33% aqueous dimethylamine solution, 10 mL of N,N-dimethylformamide (DMF) and 2.80 g of 6-chloro-N-((2-chloro-thiazole-5-yl)methyl)-N-ethyl-3-nitropyridin-2-amine, prepared according to the example 1, in 5 mL of DMF were added into a 100 mL three-necked flask equipped with a magnetic stirrer, a condenser and a drying tube, under stirring at room temperature, 1.40 g of potassium carbonate was added in batches. Reacted at the room temperature until the reaction was complete. The reaction solution was treated by the method according to example 1 to obtain 0.92 g of 6-dimethylamino-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridine-2-amine, the content of 98.0%, as a golden yellow solid in a yield of 31.4%, mp: 74.6-78.4° C., GC-MS (M+) (EI, 70 eV, m/z) calc: 341. found: 341. 1H NMR (CDCl3/TMS, 300 MHz) δ (ppm) 1.193 (t, J=7.2 Hz, 3H, CH3), 3.192 (s, 6H, 2*CH3), 3.216 (q, J=7.2 Hz, 2H, CH2), 4.811 (s, 2H, CH2), 6.022 (d, J=9.0 Hz, 1H, Py H), 7.458 (s, 1H, thiazole-H), 8.165 (d, J=9.0 Hz, 1H, Py H).
Workup
- additionwere added into a 100 mL three-necked flask
- customequipped with a magnetic stirrer, a condenser and a drying tube
- customReacted at the room temperature until the reaction
- additionThe reaction solution was treated by the method
Sources & evidence
- ORD record
- ord-17e1a01f0bdc4461a0362c8a9d3f091d
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09386769B2
Reaction notes
Loading…