Introduction of a new synthetic route about 147356-78-3

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 147356-78-3, name is N-Methoxy-N-methylcyclopropanecarboxamide, A new synthetic method of this compound is introduced below., Product Details of 147356-78-3

To a mixture of (5S,7S)-2-bromo-5-(2,5-difluorophenyl)-7-fluoro-6,7-dihydro-5H-pyrrolo[l,2- b][l,2,4]triazole (100 mg, 0.31 mmol), N-methoxy-N-methyl-cyclopropanecarboxamide (81 mg, 0.63 mmol) in tetrahydrofuran (3 mL) was added isopropylmagnesium chloride (2.0 M in tetrahydrofuran, 0.31 mL, 0.63 mmol) dropwise at 0 C. The mixture was stirred at 0 C for 0.5 h and quenched by addition of saturated aqueous ammonium chloride (10 mL). The mixture was extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with water (20 mL), brine (20 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC to give cyclopropyl-[(5S,7S)-5-(2,5-difluorophenyl)-7-fluoro-6,7-dihydro-5H- pyrrolo[l ,2-b][l,2,4]triazol-2-yl]methanone (22.1 mg, 23%) as a white solid. H NMR (400 MHz, CD3OD) delta 7.28 – 7.17 (m, 2H), 6.93 – 6.88 (m, 1H), 6.22 – 6.06 (m, 1H), 5.90 – 5.86 (m, 1H), 3.88 – 3.74 (m, 1H), 3.09 – 3.02 (m, 1H), 2.93 – 2.82 (m, 1H), 1.21 – 1.18 (m, 2H), 1.15 – 1.11 (m, 2H). LCMS RT = 1.007 min, m/z = 308.1 [M+H]+. LCMS (10 to 80%o acetonitrile in water + 0.03%o trifluoacetic acid over 2 mins) retention time 1.007 min, ESI+ found [M+H] = 308.1.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; PATEL, Snahel; HAMILTON, Gregory; ZHAO, Guiling; CHEN, Huifen; DANIELS, Blake; STIVALA, Craig; (358 pag.)WO2019/12063; (2019); A1;,
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