Water → cis-(1-(6-Amino-5-nitropyridin-2-yl)-6-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone
Reaction equation
Cl.[CH3:2][C@H:3]1[NH:8][CH2:7][C@@H:6]([C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:24]1[N:29]=[C:28]([NH2:30])[C:27]([N+:31]([O-:33])=[O:32])=[CH:26][CH:25]=1.O>C(#N)C>[NH2:30][C:28]1[N:29]=[C:24]([N:8]2[C@H:3]([CH3:2])[CH2:4][CH2:5][C@H:6]([C:9]([N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[O:10])[CH2:7]2)[CH:25]=[CH:26][C:27]=1[N+:31]([O-:33])=[O:32]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of cis-(6-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone hydrochloride (0.5 g, 2.15 mmol) in acetonitrile (10 mL) was added triethylamine (0.89 mL, 6.46 mmol). The mixture was stirred at room temperature for 10 min. Then 6-chloro-3-nitropyridin-2-amine (260 mg, 1.50 mmol) was added and the reaction mixture was stirred at 80° C. for 3 h and then at room temperature for 12 h. Water was added and the mixture was extracted with ethyl acetate. The organics were dried over sodium sulfate and concentrated under reduced pressure to afford cis-(1-(6-amino-5-nitropyridin-2-yl)-6-methylpiperidin-3-yl)(pyrrolidin-1-yl)methanone (0.5 g). MS (ES+APCI) (M+H) 334.2; LCMS retention time 4.028 min (Method S1).
Workup
- stirringthe reaction mixture was stirred at 80° C. for 3 h
- waitat room temperature for 12 h
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe organics were dried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-590f7c20874344d98a0c4bfed1ca5a77
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296745B2
Reaction notes
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