Triethylamine → HCID 89854527, compound

Reaction equation

[CH3:1][C@@H:2]1[NH:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[O:4][CH2:3]1.C(N(CC)CC)C.Cl[C:22]1[N:27]=[C:26]([NH2:28])[C:25]([N+:29]([O-:31])=[O:30])=[CH:24][CH:23]=1>CS(C)=O>[CH3:1][C@H:2]1[CH2:3][O:4][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:6][N:7]1[C:22]1[N:27]=[C:26]([NH2:28])[C:25]([N+:29]([O-:31])=[O:30])=[CH:24][CH:23]=1

Participants

Procedure

To a solution of (5S)-5-methyl-2-(pyridin-2-yl)morpholine (0.7 g, 3.93 mmol) in dimethylsulfoxide (20 mL) was added triethylamine (0.68 g, 7.86 mmol). After 10 min, 6-chloro-3-nitropyridin-2-amine (0.68 g, 3.93 mmol) was added. After 4 h at 110° C., the mixture was cooled to room temperature, and then was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via silica gel chromatography (80% ethyl acetate in petroleum ether) to afford 6-((5S)-5-methyl-2-(pyridin-2-yl)morpholino)-3-nitropyridin-2-amine (0.5 g, 41%).