Diisopropylethylamine → (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

HRID 931181Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]([N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])[CH2:2]1.C(N(C(C)C)CC)(C)C.Cl[C:24]1[N:29]=[C:28]([NH2:30])[C:27]([N+:31]([O-:33])=[O:32])=[CH:26][CH:25]=1>CN(C)C=O>[NH2:30][C:28]1[N:29]=[C:24]([N:1]2[CH2:6][CH2:5][CH2:4][C@@H:3]([C:7]([N:9]3[CH2:10][CH2:11][CH2:12][CH2:13]3)=[O:8])[CH2:2]2)[CH:25]=[CH:26][C:27]=1[N+:31]([O-:33])=[O:32]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of (R)-piperidin-3-yl(pyrrolidin-1-yl)methanone in N,N-dimethylformamide (120 mL) was added diisopropylethylamine (15 mL) followed by 6-chloro-3-nitropyridin-2-amine (3.47 g, 20 mmol). The mixture was stirred at 50° C. for 16 h. The solvent was removed under reduced pressure. The residue was purified via flash column chromatography over silica gel (ethyl acetate:petroleum ether, 1:10 to 10:1) to afford (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidine-3-yl)(pyrrolidin-1-yl)methanone (4.838 g, 76.3%).

Workup

customThe solvent was removed under reduced pressure
customThe residue was purified via flash column chromatography over silica gel (ethyl acetate:petroleum ether, 1:10 to 10:1)

Sources & evidence

ORD record: ord-b4cdc74ff0da4deba9341bffdf88d3fc
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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