Triethylamine → (R)-1-(6-amino-5-nitropyridin-2-yl)-N-ethyl-N-methylpiperidine-3-carboxamide

HRID 931140Notes

Reaction equation

[CH2:1]([N:3]([CH3:12])[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]1)=[O:5])[CH3:2].Cl[C:14]1[N:19]=[C:18]([NH2:20])[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][CH:15]=1.C(N(CC)CC)C>CS(C)=O>[NH2:20][C:18]1[N:19]=[C:14]([N:8]2[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([N:3]([CH2:1][CH3:2])[CH3:12])=[O:5])[CH2:7]2)[CH:15]=[CH:16][C:17]=1[N+:21]([O-:23])=[O:22]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (R)—N-ethyl-N-methylpiperidine-3-carboxamide (600 mg, 4.1 mmol) in dimethylsulfoxide (6 mL) were added 6-chloro-3-nitropyridin-2-amine (0.58 g, 3.3 mmol) and triethylamine (1.2 mL, 8.3 mmol) at room temperature. The reaction mixture was heated to 80° C. for 18 h. The reaction mixture was poured into ice water, extracted with ethyl acetate and concentrated under reduced pressure. The crude material was purified via column chromatography (10% ethyl acetate in petroleum ether) to afford (R)-1-(6-amino-5-nitropyridin-2-yl)-N-ethyl-N-methylpiperidine-3-carboxamide (500 mg, 28.4%). MS (ES+) (M+H) 308.31.

Workup

extractionextracted with ethyl acetate
concentrationconcentrated under reduced pressure
customThe crude material was purified via column chromatography (10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-abe0324b7fa44351be426ace233580f6
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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