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

64188-97-2

General procedure for the synthesis of 3-aminoisonicotinamide from 3-aminoisonicotinic acid: ammonium hydrochloride (4.98 g, 93.2 mmol) was mixed with 3-aminoisonicotinic acid (9.90 g, 71.7 mmol) to which was added 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1 ,1,3,3-tetramethylene diuronium hexafluorophosphate (V) ( 35.4 g, 93.2 mmol) and N-ethyl-N-isopropylpropan-2-amine (37.5 mL, 215.02 mmol) in a solution of DMF (100 mL). The reaction mixture was stirred at 40 °C for 72 h under nitrogen protection. After completion of the reaction, the solvent was removed by evaporation to give the crude product. The crude product was purified by fast silica gel column chromatography using a gradient elution with a dichloromethane solution of 5% methanol. The purified grades were collected and evaporated to dryness to give 3-aminoisonicotinamide (8.57 g, 87% yield) as a yellow gel.

7579-20-6 Synthesis

7579-20-6
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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