Propylamine → HCID 69357201, compound

HRID 852648Notes

Reaction equation

HRID 852648 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:12]=[C:11]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH:10]=[C:6]([C:7]([OH:9])=O)[CH:5]=1.C(Cl)(C(Cl)=O)=O.[CH2:26]([NH2:29])[CH2:27][CH3:28]>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:12]=[C:11]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH:10]=[C:6]([C:7]([NH:29][CH2:26][CH2:27][CH3:28])=[O:9])[CH:5]=1

Participants

6

Reactant 3

HCID 7852PropylamineHCID 65578Oxalyl chlorideHCID 69358928HCID 69358928, compound

Product 1

HCID 69357201HCID 69357201, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 5-(2-oxo-pyrrolidin-1-yl)-isophthalic acid monomethyl ester (A75) (200 mg, 76 mmol, 1 equiv) in CH2Cl2 (20 ml) at room temperature was treated with a few drops of DMF followed by (COCl)2 (100 mg, 0.8 mmol, 1.1 equiv). The resulting mixture was stirred for 1 h and then propylamine (140 mg, 2.4 mmol, 3.3 equiv) was added and the resulting solution was stirred for 30 min. The solution was then washed with 2N aqueous HCl solution (30 ml), saturated aqueous NaHCO3 solution (30 ml), dried over MgSO4 and concentrated in vacuo to give 5-(2-oxo-pyrrolidin-1-yl)-N-propyl-isophthalamic acid methyl ester (B77) (127 mg, 55%) as a cream waxy solid.

Workup

  1. stirringthe resulting solution was stirred for 30 min
  2. washThe solution was then washed with 2N aqueous HCl solution (30 ml), saturated aqueous NaHCO3 solution (30 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f135cfc43fac42968170f951ebe27551
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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