Picolinic acid → HCID 67726721, compound

HRID 1721155Notes

Reaction equation

HRID 1721155 reaction equation
[C:1]1([C@@H:7]([NH2:16])[C@@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](O)=O>CN(C1C=CN=CC=1)C.ClCCl>[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][NH:16][C@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C@@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:9]

Participants

5

Reactant 2

HCID 1018Picolinic acidHCID 2724998(1R,2R)-(+)-1,2-Diphenylethylenediamine

Product 1

HCID 67726721HCID 67726721, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (1R,2R)-1,2-diphenylethylenediamine (1.16 g, 4.74 mmol), picolinic acid (596 mg, 4.79 mmol, 1.01 eq.), N,N-dimethyl-4-aminopyridine (100 mg, 0.82 mmol, 0.17 eq.) and 1,3-dicyclohexycarbodiimide (1.07 g, 5.2 mmol, 1.1 eq.) in dichloromethane (40 ml) was stirred at room temperature under N2 for 18 hours. The reaction mixture was filtered and washed with water. Column chromatography on silica gel using EtOAc/CH2Cl2 (4:1) afforded 1.06 g of white solids as title compound (71% yield). NMR and GCMS confirmed the structure.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-07570611b70f4f08ae65f215b2d25557
Source dataset
uspto-grants-1996_04
Patent number
US05508458

Reaction notes

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