Picolinic acid → HCID 67726721, compound

HRID 1450698Notes

Reaction equation

HRID 1450698 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-b24b6ec16135467e97f28d54c0cc0ede
Source dataset
uspto-grants-1997_02
Patent number
US05602267

Reaction notes

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