41716-18-1, A common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
e) {(S)-3-[4-(5-Amino-6-methoxy-pyridin-3-yl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yloxy]-pyrrolidin-1-yl}-(1-methyl-1H-imidazol-4-yl)-methanone A solution of 1-methyl-1H-imidazole-4-carboxylic acid (CAS registry 41716-18-1) (36.0 mg, 0.26 mmol) and Et3N (0.11 ml, 0.78 mmol) in DMF (1 ml) was treated with HBTU (CAS registry 94790-37) (107 mg, 0.28 mmol). After stirring at rt for 20 min, the reaction mixture was cooled down to 5¡ã C. and a solution of 2-methoxy-5-[6-((S)-pyrrolidin-3-yloxy)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-pyridin-3-ylamine (88 mg, 0.26 mmol) in DMF (3 ml) was added. The reaction mixture was stirred at rt for 1 h, concentrated and the residue was taken up in DCM (10 ml), washed with a sat. aq. NaHCO3 soln. (5 ml), the organic layer was separated by elution through a separating phase cartridge and concentrated. The residue was purified by flash chromatography on silica gel (heptane/EtOAc 100:0 to 0:100), the combined fractions were concentrated, dissolved in tBuOH/H2O and lyophilized to afford the title compound as a colourless solid (21 mg, 37percent yield). UPLC RtM2=0.85 min; ESIMS: 451 [(M+H)+]. 1H NMR (400 MHz, CD3OD): delta 7.64 (s, 1H), 7.62 (s, 1H), 7.65 m, 1H), 6.93 (m, 1H), 6.70 (m, 1H), 6.20-6.34 (m, 1H), 6.15 (m, 1H), 4.81 (m, 1H), 4.19-4.31 (m, 2H), 3.90-4.05 (m, 4H), 3.55-3.83 (m, 8H), 2.04-2.28 (m, 2H).
The synthetic route of 41716-18-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; NOVARTIS AG; CARAVATTI, Giorgio; CHAMOIN, Sylvie; FURET, Pascal; HOGENAUER, Klemens; HURTH, Konstanze; KALIS, Christoph; KAMMERTOENS, Karen; LEWIS, Ian; MOEBITZ, Henrik; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; WOLF, Romain; ZECRI, Frederic; US2013/165436; (2013); A1;,
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