14064-10-9, name is Diethyl 2-chloromalonate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C7H11ClO4
[00788] (i) Production of ethyl 4-hydroxy-2-(2-methylpyrazolo[l,5-a]pyridin-3-yl)-l,3-thiazole-5- carboxylate and ethyl 4-ethoxy-2-(2-methylpyrazolo[l,5-a]pyridin-3-yl)-l,3-thiazole-5-carboxylate [00789] A suspension of 2-methylpyrazolo[l,5-a]pyridine-3-carbothioamide hydrochloride (1.7 g, 7.5 mmol) produced in Example 11-B (v) and diethyl chloromalonate (2.0 g, 11 mmol) in 2-propanol (25 mL) was stirred at 900C for 4 hr with heating. The reaction mixture was cooled to room temperature, and MPI09-013Pl RNWOM PCT FILING the precipitated solid was collected by filtration and dried to give ethyl 4-hydroxy-2-(2- methylpyrazolo[1.5-a]pyridin-3-yl)-l,3-thiazole-5-carboxylate (1.45 g, 64percent) as a yellow solid.[00790] 1H-NMR (DMSO-d6, 300 MHz) delta 1.27 (3H, t, J = 7.1 Hz), 2.65 (3H, s), 4.23 (2H, q, J = 7.1Hz), 7.12 (IH, dt, J = 1.3, 6.8 Hz), 7.51 – 7.65 (IH, m), 8.36 (IH, d, J = 8.9 Hz), 8.79 (IH, d, J = 6.8 Hz),11.76 (IH, s).00791] Saturated aqueous sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL) were added to the filtrate, and the mixture was stirred for 30 min. The organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to give ethyl 4-ethoxy-2-(2- methylpyrazolo[l,5-a]pyridin-3-yl)-l,3-thiazole-5-carboxylate (200 mg, 32percent) as a yellow solid.[00792] 1H-NMR (DMSO-d6, 300 MHz) delta 1.27 (3H, t, J = 7.1 Hz), 1.42 (3H, t, J = 6.9 Hz), 2.65 (3H, s), 4.23 (2H, q, J = 7.1 Hz), 4.61 (2H, q, J = 6.9 Hz), 7.12 (IH, dt, J = 1.3, 6.9 Hz), 7.55 – 7.69 (IH, m),8.32 (IH, d, J = 8.9 Hz), 8.79 (IH, d, J = 6.9 Hz).
The synthetic route of 14064-10-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BANNO, Hiroshi; HIROSE, Masaaki; KURASAWA, Osamu; LANGSTON, Steven, P.; MIZUTANI, Hirotake; SHI, Zhan; VISIERS, Irache; VOS, Tricia, J.; VYSKOCIL, Stepan; WO2010/90716; (2010); A1;,
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