NSC-703786 synthesis
- Product Name:NSC-703786
- CAS Number:260443-89-8
- Molecular formula:C14H11FN2S
- Molecular Weight:258.31
![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
1000210-73-0
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260443-89-8
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Yield: 48%
Reaction Conditions:
with tin(II) chloride hydrate in ethanol for 3 h;Reflux;
Steps:
4-(5-fluorobenzothiazol-2-yl)-2-methylaniline (5F203)
1d(3.0 g, 10.42 mmol) was suspended in ethanol (50 mL) and then tin (II) chloridedihydrate (11.752 g, 52.0 mmol) was added and the reaction mixture was heatedunder reflux for 3 hours. The solvent was removed under reduced pressure toyield a brown oil. The residue was taken up into EtOAc (240 mL) and washed with2M NaOH (2 x 70 mL), H2O (35 mL) and brine (10 mL). The organiclayer was dried over Na2SO4 and the solvent was removed underreduced pressure to yield a brown solid. The crude product was purified bysilica gel flash chromatography (gradient method, 0.5%-2% MeOH in CH2Cl2)to afford 5F203 as ayellow solid (1.30 g, 48 % yield). 1H NMR (400 MHz, DMSO-d6): δ 8.03 (dd, J=5.5, 8.8 Hz, 1H, H-7), 7.71 (dd, J=2.5, 10.1 Hz, 1H, H-4), 7.67 (d, J=1.9 Hz, 1H, H-2’), 7.63 (dd, J=2.4,8.3 Hz, 1H, H-6’), 7.23 (td, J=2.7,9.1 Hz, 1H, H-6), 6.70 (d, J=8.4 Hz,1H, H-5’), 5.72 (bs, 2H, NH2), 2.14 (s, 3H, CH3). 13CNMR (100 MHz, DMSO-d6): 171.03, 162.51, 160.13, 154.89, 150.65, 129.23, 126.60,123.06, 121.01, 120.06, 113.59, 112.45, 107.77, 17.31. MS: m/z (HRMS)calcd. for C14H12FN2S+ 259.0700[M+H], MS found: 259.0522 [M+H]. Analytical RP-HPLC tR= 18.26 minutes.
References:
Stone, Erica L.;Citossi, Francesca;Singh, Rajinder;Kaur, Balvinder;Gaskell, Margaret;Farmer, Peter B.;Monks, Anne;Hose, Curtis;Stevens, Malcolm F.G.;Leong, Chee-Onn;Stocks, Michael;Kellam, Barrie;Marlow, Maria;Bradshaw, Tracey D. [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 21,p. 6891 - 6899] Location in patent:supporting information
35675-46-8
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1000210-73-0
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343975-60-0
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1003-99-2
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260443-89-8
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