In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 176969-34-9 as follows. SDS of cas: 176969-34-9
anti-Enriched 5-amino-9-isopropyl-benzonorbornene (42g, syn/anti-ratio 3:7; prepared as described in WO 04/35589 or WO 06/37632) was chromatographed on silica gel (2.1kg ) in ethyl acetate-hexane-(1:7). The last eluting fractions with antf-contents > 97% (1.2 g, g.l.c) were combined and rechromatographed on silica gel (25Og) in ethyl acetate to give 0.72g (1.96%) of a crystalline solid (m.p. 64 0C) with an antf-content of 99.2% (g.l.c).5-Amino-9-anNo.-isopropyl-benzonorbornene (0.72g, 99.2% anti, prepared as described above) was reacted with 5-difluoromethyl-2-methyl-pyrazole-4-carboxylic acid (0.76g, 1.2 eq.)tau bis-(2-oxo-3-oxazolidinyl)-phosphinic acid chloride (1.Og, 1.2 eq.) and triethylamine (0.87g, 2.4 eq.) in dichloromethane (25ml) at room temperature for 3h to give after aqueous work up with saturated NaHCO3-solution and purification on silica gel in ethyl acetate-hexane-(1 :2 ) a viscous oil. Crystallization from hexane afforded the desired product (1.18g, yield: 91.7%, m.p. 140 0C, 99.4% anti (g.l.c)). The crystalline material was analyzed by differential scanning calorimetry and x-ray diffraction and was identified as crystal modification I of anti-3-difluoromethyl-1-methyl-1 H-pyrazole-4- carboxylic acid (9-isopropyl-1 ,2,3,4-tetrahydro-1 ,4-methano-naphthalen-5-yl)-amide no presence of other crystalline forms was detected (see figures 4, 5 and 6).
According to the analysis of related databases, 176969-34-9, the application of this compound in the production field has become more and more popular.
Reference:
Patent; SYNGENTA LIMITED; SYNGENTA PARTICIPATIONS AG; WO2008/113447; (2008); A2;,
Pyrazole – Wikipedia,
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