ChemicalBook CAS DataBase List 3-AMINO-4-PYRIDINECARBOXAMIDE

3-AMINO-4-PYRIDINECARBOXAMIDE synthesis

6synthesis methods

Product Name:3-AMINO-4-PYRIDINECARBOXAMIDE
CAS Number:64188-97-2
Molecular formula:C6H7N3O
Molecular Weight:137.14

7579-20-6 Synthesis

7579-20-6
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$10.00/1g

64188-97-2
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$8.00/100mg

Yield: 87%

Reaction Conditions:

with ammonium chloride;N-ethyl-N,N-diisopropylamine;HATU in N,N-dimethyl-formamide at 40; for 72 h;Inert atmosphere;

Steps:

3-Aminoisonicotinamide5 22
Ammonium hydrochloride (4.98 g, 93.2 mmol) was added to 3-aminoisonicotinic acid (9.90g, 71.7 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (35.4 g, 93.2 mmol) and N-ethyl-N-isopropylpropan-2-amine (37.5mL, 215.02 mmol) in DMF (100 mL) under nitrogen. The resulting solution was stirred at 40 °C for 72 hours. The mixture was evaporated to provide the crude material. The crude product was purified by flash silica chromatography with elution gradient 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford 3-aminoisonicotinamide (8.57 g, 87 %) as a yellow gum.

References:

Holmes, Jane L.;Almeida, Lynsie;Barlaam, Bernard;Croft, Rosemary A.;Dishington, Allan P.;Gingipalli, Laksmaiah;Hassall, Lorraine A.;Hawkins, Janet L.;Ioannidis, Stephanos;Johannes, Jeffrey W.;McGuire, Thomas M.;Moore, Jane E.;Patel, Anil;Pike, Kurt G.;Pontz, Timothy;Wu, Xiaoyun;Wang, Tao;Zhang, Hai-Jun;Zheng, Xiaolan [Synthesis,2016,vol. 48,# 8,art. no. SS-2015-T0725-OP,p. 1226 - 1234] Location in patent:supporting information