Synthetic Route of 920006-32-2,Some common heterocyclic compound, 920006-32-2, name is 1-Isopropylpyrazole-5-carboxylic Acid, molecular formula is C7H10N2O2, 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.
1-(propan-2-yl)-1H-pyrazole-5-carboxylic acid (37.8 mg, 245 pmol), HATU (108 mg, 283 pmol), and N,N-diisopropylethylamine (99 mI, 570 mihoI), were dissolved in 3 mL of the N,N-dimethylformamide and the resulting mixture was stirred at room temperature for 15 min, then tert-butyl 3-amino-5-(3,5-dicyano-1,2,6-trimethyl-1,4-dihydropyridin-4-yl)-7-ethyl-6-fluoro-1H-indazole-1-carboxylate (100 mg, 85 % purity, 189 pmol) was added and the resulting mixture was stirred at 90 C for 16 h. The resulting mixtur e was diluted by addition of water and extracted with ethyl acetate, the combined organic phases was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by prep-HPLC (Column: XBridge Prep C18 OBD Column 19x150mm, 5 pm; Mobile Phase A: Water (10 mmol/L NH4HC03), Mobile Phase B: ACN; Flow rate: 20 mUmin; Gradient: 25% B to 65% B in 7 min; Detector: 254 nm, 220 nm) to give 39.9 mg (43% yield) of the product as a light yellow solid. LC-MS [Water(0.05%TFA)-Acetonitrile, 5%B]: Rt = 1 .38 min. MS (ESIpos): m/z = 487 (M+H)+. 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 1 .24 (t, 3H), 1 .44 (d, 6H), 2.23 (s, 6H), 2.90 (q, 2H), 3.20 (s, 3H), 4.66 (s, 1H), 5.50-5.56 (m, 1H), 7.16 (s, 1H), 7.53-7.55 (m, 1H), 7.59 (s, 1H), 10.85 (s, 1H), 13.12 (s, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Isopropylpyrazole-5-carboxylic Acid, its application will become more common.
Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; HEINRICH, Tobias; CHRIST, Clara; BRIEM, Hans; FARIA ALVARES DE LEMOS, Adelaide, Clara; BADER, Benjamin; HOLTON, Simon; BOeMER, Ulf; LIENAU, Philip; KUHNKE, Lara, Patricia; (122 pag.)WO2019/185525; (2019); A1;,
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