| Identification | More | [Name]
Methyl 2-aminonicotinate | [CAS]
14667-47-1 | [Synonyms]
2-AMINO-NICOTINIC ACID METHYL ESTER
METHYL 2-AMINONICOTINATE
RARECHEM AL BF 1234
Methyl 2-aminopyridine-3-carboxylate
2-METHYL-4-(TRIFLUOROMETHYL)-5-AMINOTHIAZOLE
2-Amino-3-pyridinecarboxylic acid methyl ester
2-Aminopyridine-3-carboxylic acid methyl ester | [EINECS(EC#)]
681-092-5 | [Molecular Formula]
C7H8N2O2 | [MDL Number]
MFCD00128872 | [Molecular Weight]
152.15 | [MOL File]
14667-47-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
82-86 °C | [Boiling point ]
251.3±20.0 °C(Predicted) | [density ]
1.238±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
4.71±0.36(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C7H8N2O2/c1-11-7(10)5-3-2-4-9-6(5)8/h2-4H,1H3,(H2,8,9) | [InChIKey]
NZZDEODTCXHCRS-UHFFFAOYSA-N | [SMILES]
C1(N)=NC=CC=C1C(OC)=O | [CAS DataBase Reference]
14667-47-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
2 | [HazardClass ]
IRRITANT | [HS Code ]
2933399990 |
| Hazard Information | Back Directory | [Chemical Properties]
Off white powder | [Uses]
Methyl 2-Aminonicotinate is used to prepare 2-{4-[(3S)-Piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide (MK-4827)as a novel oral poly(ADP-ribose)polymerase (PARP) inhibitor efficacious in BRCA-1 and -2 mutant tumors. It is also used to synthesize quinazolinone/quinazoline thione derivatives as phosphodiesterase 7 inhibitors. | [Synthesis]
Concentrated sulfuric acid (96%, 144 mL, 2.69 mol, 18.6 eq.) was slowly added dropwise to a stirred suspension of 2-aminonicotinic acid (20.0 g, 0.145 mol) in methanol (228 mL, 7.12 mol, 49.2 eq.), and the reaction system was kept at 0 °C. Subsequently, the reaction mixture was irradiated in a microwave reactor (power input 300 W) at 60 °C and atmospheric pressure for 1.5 hours. Upon completion of the reaction, the light brown mixture was carefully poured into ice water, maintained at 0 °C, and solid sodium carbonate was added by batchwise addition until complete neutralization (pH > 8). The aqueous layer was extracted three times with ethyl acetate. The organic layers were combined, washed sequentially with saturated brine and deionized water, and then dried with anhydrous magnesium sulfate. Finally, the organic solvent was evaporated to afford methyl 2-aminopyridine-3-carboxylate (21.15 g, 93% yield) as colorless needle-like crystals with purity meeting the analytical requirements. | [References]
[1] Tetrahedron, 2014, vol. 70, # 35, p. 5541 - 5549
[2] European Journal of Medicinal Chemistry, 2012, vol. 52, p. 284 - 294
[3] Synthetic Communications, 2006, vol. 36, # 2, p. 181 - 186
[4] Patent: WO2005/32481, 2005, A2. Location in patent: Page/Page column 38
[5] Patent: WO2005/32481, 2005, A2. Location in patent: Page/Page column 38 |
|
|