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

HRID 931183Notes

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.[NH:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]([N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:19])[CH2:13]1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[NH2:8][C:6]1[N:7]=[C:2]([N:12]2[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]([N:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)=[O:19])[CH2:13]2)[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 6-chloro-3-nitropyridin-2-amine (0.175M, 20 mL, 3.5 mmol) in anhydrous N,N-dimethylformamide was added to (R)-piperidin-3-yl(pyrrolidin-1-yl)methanone, followed by diisopropylethylamine (1.3 mL, 7.0 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 preparative HPLC to afford (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidine-3-yl)(pyrrolidin-1-yl)methanone (1.0 g, 89.6%).

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified via preparative HPLC

Sources & evidence

ORD record: ord-099f291ba60f42b284fdfa996b702d46
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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