658-89-9, A common heterocyclic compound, 658-89-9, name is 4-(Trifluoromethoxy)benzene-1,2-diamine, molecular formula is C7H7F3N2O, its 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.
Step 1. Preparation of 83-1: HATU (3.06 g, 8.05 mmol) was added slowly to a solution of 3,3-difluoro-2-oxopent-4-enoic acid (1 .03 g, 6.86 mmol) in 10 mLof DMF. A mixture of 4-(trifluoromethoxy)benzene-1 ,2-diamine (1 .29 g, 6.71 mmol) and DIPEA (1.4 mL, 8.05 mmol) in 12 mL of DMF was then added. After stirring overnight, reaction mixture was poured into 175 mL of water and extracted with ethyl acetate (4 x 100 mL). Combined organics were washed with 50% brine, dried over anhydrous Na2504, filtered, and concentrated underreduced pressure. Resulting solid was purified via silica gel column chromatography (0-25% ethyl acetate in hexanes)to yield intermediate 83-1, the late eluting product. LCMS-ESI (m/z): [Mi-H] calcd for C12H8F5N202: 307.04; found: 307.29.
The synthetic route of 658-89-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GILEAD SCIENCES, INC.; BJORNSON, Kyla; CANALES, Eda; COTTELL, Jeromy, J.; KARKI, Kapil, Kumar; KATANA, Ashley, Anne; KATO, Darryl; KOBAYASHI, Tetsuya; LINK, John, O.; MARTINEZ, Ruben; PHILLIPS, Barton, W.; PYUN, Hyung-jung; SANGI, Michael; SCHRIER, Adam, James; SIEGEL, Dustin; TAYLOR, James, G.; TRAN, Chinh, Viet; TREJO MARTIN, Teresa, Alejandra; VIVIAN, Randall, W.; YANG, Zheng-Yu; ZABLOCKI, Jeff; ZIPFEL, Sheila; WO2014/8285; (2014); A1;,
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