Related Products of 16034-48-3,Some common heterocyclic compound, 16034-48-3, name is 1-Pyrazoleacetic Acid, molecular formula is C5H6N2O2, 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.
[0462] A solution of Example 1G and DIPEA (0.15 M and0.43 M in DMA, respectively, 257 f.LL, 0.04 mmol Example1 G (1.0 equivalent) and0.12 mmol DIPEA (3.0 equivalents)),HATU (0.2 M in DMA, 257 f.LL, 0.052 mmol, 1.3 equivalents),and 2-(1H-pyrazol-1-yl)acetic acid (0.40 Min DMA,121 f.LL, 0.048 mmol, 1.2 equivalents) were aspirated fromtheir respective source vials, mixed through a perfluoroalkoxymixing tube (0 2 mm inner diameter), and loaded intoan injection loop. The reaction segment was injected into theflow reactor (Hastelloy coil, 0.75 mm inner diameter, 1.8 mLinternal volume) set at 100 C., and passed through the reactorat 180 fJ.Lmin- 1 (10 minute residence time). Upon exiting thereactor, the reaction was loaded directly into an injection loopand purified by preparative HPLC on a Phenomenex LunaC8(2) 5 flill 100 A AXIA colunm (50 mmx21.2 mm) Agradient of acetonitrile (A) and 0.1% ammonium acetate inwater (B) was used, at a flow rate of30 mLmin (0-0.5 min 5%A, 0.5-6.5 min linear gradient 5-60% A, 6.5-7.0 min lineargradient 60-100%A, 7.0-8.9 min 100%A, 8.9-9.0minlineargradient 100-5%A, 9.0-10 min 5%A) to yield the title com-pound (7.33 mg, 39% yield). 1H NMR (400 MHz, DMSOd6D20)o7.76 (d, 1=2.3 Hz, lH), 7.60-7.45 (m, 4H), 7.37-7.28 (m, lH), 7.07-6.87 (m, 3H), 6.31 (t, 1=2.1 Hz, lH), 5.82 (s,lH), 5.00 (s, 2H), 3.93 (q, 1=6.9 Hz, 2H), 3.36 (s, 3H), 1.14 (t,1=6.9 Hz, 3H). MS (ESI) m/z 481.1 (M+W).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Pyrazoleacetic Acid, its application will become more common.
Reference:
Patent; Bogdan, Andrew; Kati, Warren M.; McDaniel, Keith F.; Park, Chang H.; Sheppard, George S.; Wang, Le; US2015/158873; (2015); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics