Pipecolic Acid → HCID 67060270, compound

HRID 1625106Notes

Reaction equation

HRID 1625106 reaction equation
[NH:1]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:2]1[C:3]([OH:5])=O.[CH3:10][O:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[N:21]=[C:22]=[O:23].[OH-].[Na+]>C1COCC1>[CH3:10][O:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[N:21]1[C:3](=[O:5])[CH:2]2[CH2:6][CH2:7][CH2:8][CH2:9][N:1]2[C:22]1=[O:23]

Participants

5

Reactant 3

HCID 849Pipecolic AcidHCID 14798Sodium HydroxideHCID 34920221-isocyanato-2-methoxy-4-nitrobenzene

Product 1

HCID 67060270HCID 67060270, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of pipecolinic acid (500 mg; 3.87 mmol), 2-methoxy-4-nitrophenylisocyanate (902 mg; 4.65 mmol) and 9:1 THF:2 M NaOH were reacted in a microwave vessel at 160° C. for 10 min. The reaction mixture was then cooled to rt and purified by column chromatography (1:1, EtOAc:hexanes) to afford 736 mg of 2-(2-methoxy-4-nitrophenyl)tetrahydroimidazo[1,5-a]pyridine-1,3(2H,5H)-dione, 1.1.1, (62%).

Workup

  1. custompurified by column chromatography (1:1, EtOAc:hexanes)

Sources & evidence

ORD record
ord-25b005f1718b4bc0847b8774245bd61a
Source dataset
uspto-grants-2014_07
Patent number
US08779157B2

Reaction notes

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