Electric Literature of 210532-25-5,Some common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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.
General procedure: 4-(6-(3-aminophenyl)-2,3-dihydroimidazo[2,l-b]thiazol-5-yl)-N-(4-(4-ethylpiperazin-l- yl)phenyl)pyrimidin-2-amine (compound of Step lh, 0.1 g) was dissolved in NMP and 2- naphthoyl chloride (42 mg, 0.220 mM) was added to the reaction mixture. The reaction mixture was stirred at RT for lh. The reaction mixture was diluted with diethyl ether, stirred for 5 min and ether was removed. The dilution of the reaction mixture with diethyl ether and removal of ether was repeated twice. The reaction mixture was further diluted with DCM and washed with aqueous saturated NaHC03. The organic layer was dried over anhydrous Na2S04, concentrated to yield crude product which was purified by flash column chromatography (silica gel, eluted with 6% MeOH in DCM) to afford the title compound ((4-(4-ethylpiperazin-l- yl)phenyl)amino)pyrimidin-4-yl)-2,3-dihydroimidazo[2, 1 -b]thiazol-6-yl)phenyl)-2-naphthamide. Yield: 0.069 g (53%); (0492) ‘H NMR (CDC13, 300 MHz): delta 8.56 (s, IH), 8.46 (s, IH), 8.19-8.17 (d, J=5.7 Hz, IH), 8.00-7.97 (m, 3H), 7.92-7.90 (d, J=6.6Hz, IH), 7.83 (s, IH), 7.62-7.58 (m, 2H), 7.50-7.47 (d, J=8.4 Hz, 2H), 7.42-7.36 (m, 3H), 6.92-6.89 (d, J=8.7 Hz, 2H), 6.74-6.72 (d, J=5.7 Hz, IH), 4.54-4.49 (t, J=6.9 Hz, 2H), 3.870-3.82 (t, J=6.9 Hz, 2H), 3.57 (m, 4H), 3.16 (m,4H), 2.54-2.52 (m, 2H), 1.17- 1.15 (t, J= 6.9Hz, 3H); MS: m/z 653.5 (M+l).The title compound was prepared in an analogous manner as the compound 1 of Example 1 involving reaction of 4-(6-(3-aminophenyl)-2,3-dihydroimidazo[2,l-b]thiazol-5-yl)-N-(4-(4- ethylpiperazin-l-yl)phenyl)pyrimidin-2-amine (Step lh of Example 1) with 3,5-difluorobenzene- 1 -sulphonyl chloride in DCM in the presence of pyridine at RT for lh. Yield: 75.7%; (0625) 1H NMR (DMSO-d6, 300 MHz): delta 10.57 (br s,lH), 9.58 (s, IH), 9.44 (s, IH), 8.19 (d, J=5.1 Hz, IH), 7.65 (d, J=12 Hz, IH), 7.57-7.55 (d, J=5.4 Hz, IH), 7.41 (s, IH), 7.33-7.17 (m, 6H), 6.95- 6.93 (d, J=5.7 Hz, 2H), 6.40-6.38 (d, J=6 Hz, IH), 4.59-4.55 (t, J=6 Hz, 2H), 4.19-4.17 (t, J=6 Hz, 2H), 3.7 (d, J=12 Hz, 2H), 3.21-3.13 (m, 5H), 2.90-2.80 (m, 3H), 1.25 (t, J=6 Hz, 3H); m/z 672.6 (M+l).
The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; PIRAMAL ENTERPRISES LIMITED; ROYCHOWDHURY, Abhijit; SHARMA, Rajiv; GADEKAR, Pradip, Keshavrao; URUNKAR, Ganesh, Devidas; SEELABOYINA, Balapadmasree; DEKA, Nabajyoti; DAWANGE, Mahesh, Balasaheb; B-RAO, Chandrika; KHANNA, Smriti; WO2015/128698; (2015); A1;,
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