Dimethylformamide → (R)-1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylic acid

HRID 931197Notes

Reaction equation

HRID 931197 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.CN(C)C=O.[NH:17]1[CH2:22][CH2:21][CH2:20][C@@H:19]([C:23]([OH:25])=[O:24])[CH2:18]1.C(N(C(C)C)CC)(C)C>>[NH2:8][C:6]1[N:7]=[C:2]([N:17]2[CH2:22][CH2:21][CH2:20][C@@H:19]([C:23]([OH:25])=[O:24])[CH2:18]2)[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 1796510(-)-Nipecotic acidHCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

HCID 89853836(R)-1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylic acid

Conditions

Temperature
80 °C

Procedure

A solution of 6-chloro-3-nitropyridin-2-amine in N,N-dimethylformamide (70 mL, 12.25 mmol, 0.175M) was added to (R)-piperidine-3-carboxylic acid (12.25 mmol) followed by diisopropylethylamine (4.55 mL, 24.5 mmol). The reaction mixture was stirred at 80° C. for 16 h. The solvent was removed under reduced pressure to afford (R)-1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylic acid which was used without further purification.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2f00c391f76448ad97a74f318022d5e0
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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