Water → (R)-1-(6-amino-5-nitropyridin-2-yl)-N,N-dimethylpiperidine-3-carboxamide

HRID 931122Notes

Reaction equation

[CH3:1][N:2]([CH3:11])[C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][NH:7][CH2:6]1)=[O:4].C(N(CC)CC)C.Cl[C:20]1[N:25]=[C:24]([NH2:26])[C:23]([N+:27]([O-:29])=[O:28])=[CH:22][CH:21]=1.O>CS(C)=O>[NH2:26][C:24]1[N:25]=[C:20]([N:7]2[CH2:8][CH2:9][CH2:10][C@@H:5]([C:3]([N:2]([CH3:11])[CH3:1])=[O:4])[CH2:6]2)[CH:21]=[CH:22][C:23]=1[N+:27]([O-:29])=[O:28]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of (R)—N,N-dimethylpiperidine-3-carboxamide (10 g, 64.04 mmol) in dimethylsulfoxide (100 mL) were added triethylamine (17.8 mL, 128.08 mmol) and 6-chloro-3-nitropyridin-2-amine (7.76 g, 44.82 mmol) at room temperature under a nitrogen atmosphere. The reaction mixture was heated at 110° C. for 16 h. The reaction mixture was added to cold water and extracted with ethyl acetate. The organic layer was washed with cold water 3 times, dried over sodium sulfate and evaporated under reduced pressure. The crude compound was purified via flash chromatography and then treated with 1:1 petroleum ether and diethyl ether to afford (R)-1-(6-amino-5-nitropyridin-2-yl)-N,N-dimethylpiperidine-3-carboxamide (11 g, 72%). MS (ES+APCI) (M+H) 294.1; LCMS retention time: 2.777 min (Method E1)

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with cold water 3 times
dry with materialdried over sodium sulfate
customevaporated under reduced pressure
customThe crude compound was purified via flash chromatography
additiontreated with 1:1 petroleum ether and diethyl ether

Sources & evidence

ORD record: ord-ddf4aff28f1c484390874b672e0b35a4
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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