Triethylamine → 3-[2-(Methoxycarbonyl)acetylamino]pyridine-4-carboxylic acid

HRID 1882883Notes

Reaction equation

HRID 1882883 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].Cl[C:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:13].C(N(CC)CC)C>CC(C)=O>[CH3:18][O:17][C:15]([CH2:14][C:12]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9])=[O:13])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123460Methyl malonyl chlorideHCID 4595313-Aminoisonicotinic acid

Product 1

HCID 129887813-[2-(Methoxycarbonyl)acetylamino]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-aminopyridine-4-carboxylic acid (1.0 eq), methyl 2-(chlorocarbonyl)acetate (1.1 eq), and triethylamine (2.0 eq) in acetone was stirred overnight at room temperature. The solvent was removed in vacuo. The product was used without further purification. LC/MS m/z 239.2 (MH+), Rt 1.40 minutes.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe product was used without further purification

Sources & evidence

ORD record
ord-430d32fa1cca4af288744e014f6b8b67
Source dataset
uspto-grants-2004_07
Patent number
US06759417B2

Reaction notes

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