Picolinic acid → HCID 7184161, compound

HRID 230793Notes

Reaction equation

HRID 230793 reaction equation
C(N(C(C)C)CC)(C)C.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]([OH:18])=O.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.CN(C=O)C>[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]([NH:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:25]=1)=[O:18]

Participants

7

Reactant 4

HCID 1018Picolinic acidHCID 12082Methyl 4-aminobenzoateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 7184161HCID 7184161, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Diisopropylethylamine (2.3 mL) was added to a DMF solution (15 mL) of picolinic acid (814 mg), methyl 4-aminobenzenecarboxylate (1.0 g) and HATU (2.8 g), and stirred overnight at room temperature. Water was added to the reaction solution, and the resulting precipitate was taken out through filtration. The obtained residue was purified through silica gel column chromatography (chloroform/methanol=500/10 to 500/15) to obtain the entitled compound (1.4 g).

Workup

  1. filtrationthe resulting precipitate was taken out through filtration
  2. customThe obtained residue was purified through silica gel column chromatography (chloroform/methanol=500/10 to 500/15)

Sources & evidence

ORD record
ord-da3daba8549147bc9128292c10e68d8f
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

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