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

HRID 931188Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12][N:13]([CH3:22])[C:14]([C@@H:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1)=[O:15].C(N(CC)CC)C>CN(C)C=O>[NH2:8][C:6]1[N:7]=[C:2]([N:18]2[CH2:19][CH2:20][CH2:21][C@@H:16]([C:14]([N:13]([CH3:22])[CH3:12])=[O:15])[CH2:17]2)[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-chloro-3-nitropyridin-2-amine (4.15 g, 24.0 mmol) in N,N-dimethylformamide (41 mL) was added (R)—N,N-dimethylpiperidine-3-carboxamide (3.74 g, 2.40 mmol) followed by triethylamine (10.7 mL, 64.800 mmol). The reaction mixture was stirred at 80° C. for 16 h. The solvent was removed under reduced pressure and the residue was purified via column chromatography to afford (R)-1-(6-amino-5-nitropyridin-2-yl)-N,N-dimethylpiperidine-3-carboxamide.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified via column chromatography

Sources & evidence

ORD record: ord-37e74191845f4ee4ba2c97917145ee13
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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