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Chemical Structure| 335255-43-1
Chemical Structure| 335255-43-1
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CAS No. :335255-43-1 MDL No. :MFCD24038830
Formula : C15H18N2O2S Boiling Point : -
Linear Structure Formula :- InChI Key :JNJJINIJWXHEQQ-UHFFFAOYSA-N
M.W : 290.38 Pubchem ID :57717474
Synonyms :

Safety of [ 335255-43-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 335255-43-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 335255-43-1 ]
  • Downstream synthetic route of [ 335255-43-1 ]

[ 335255-43-1 ] Synthesis Path-Upstream   1~4

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  • [ 335255-43-1 ]
YieldReaction ConditionsOperation in experiment
100% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 2 h; General procedure: Synthesis oftert-butyl (2-amino~4-(thiophen-2-yl)phenyl)carbamate (9a):Compound 9a was made following the procedure reported in the patent literature ( WO 2009/055917). Compound 8a (0.24 g. 0.75 mmol) was placed in a round bottom flask and 10percent palladium on carbon (catalytic amount, 20 mg) was added into it. The reaction mixture was exposed to a balloon. After purging with the reaction mixture was stirred under balloon for 2 hours at room temperature. It was then filtered through Ceiite and concentrated under vacuum to give the desired amine (0.217 g, 100percent yield).lE NMR (400 MHz, Chloroform-d) δ 7.33 - 7.27 (m, 1H), 7.25 - 7.21 (m, 2H)57.08 - 7.03 (m, 2H), 7.02 (d, J= 2.0 Hz, 1H), 1.52 (s, 9H).
98% With palladium on activated charcoal; hydrogen In methanol; ethyl acetate at 20℃; for 20 h; 4.1.8.1. tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate (16a). Compound 15a (0.53 g, 1.66 mmol) was solubilized in methanol and EtOAc (6 + 16 mL) and stirred at room temperature for 20 h with Pd/C (0.05 g, 10percent w/w) under hydrogen atmosphere. The catalyst was filtered off, and the solvent was removed and washed with PE to give compound 16a as a white solid (0.47 g, 98percent yield). 1H NMR (400 MHz, DMSO-d6) δ 8.34 (s, 1H), 7.44-7.42 (m, 1H), 7.29 (dd, J = 3.5, 1.2 Hz, 1H), 7.26 (d, J = 8.5 Hz, 1H), 7.11 (dd, J = 5.3, 3.5 Hz, 1H), 6.97 (d, J = 2.0 Hz, 1H), 6.78 (dd, J = 8.5, 2.2 Hz, 1H), 5.04 (s, 2H), 1.45 (s, 9H).
95% With hydrogen In ethyl acetate at 20℃; for 18 h; Step 3 : tert-Butyi 2-amino-4-(thiophen-2-yl)phenylcarbamate (4); [0679] Compound 3 was suspended in AcOEt and placed under nitrogen atmosphere; then10percent palladium on carbon (catalytic amount) was added. The reaction mixture was placed under vacuum for a few min then opened up under a balloon of hydrogen and stirred at ambient temperature for 18 h. The reaction mixture was filtered through Celite.(R). and concentrated to give compound 4 (0.393 g, 95percent yield).[0680] 1H NMR (DMSO-d6 δ (ppm): 8.33 (s, IH), 7.42 (dd, J= 4.9, 0.98 Hz, IH), 7.27 (dd,J= 3.5, 0.98 Hz, IH), 7.06 (dd, J= 5.1, 3.7 Hz, IH), 6.95 (d, J= 2.2 Hz, IH), 6.82 (dd, J= 8.0 Hz,2.0 Hz, IH), 5.01 (s, 2H), 1.47 (s, 9H).
85% With palladium on activated charcoal; hydrogen In methanol To a solution of 40a (3.43 g, 10 mmol) in CH3OH (200 mL),was added dry palladium-carbon (0.34 g), the mixture was stirredunder a hydrogen atmosphere overnight. The palladium-carbonwas filtered off over celite, after evaporating the solvent, the residuewas dried under vacuum to give 41a (2.46 g, 85percent), a whitesolid. 1H NMR (400 MHz, DMSO-d6) δ 8.35 (s, 1H), 7.45-7.43 (m,1H), 7.30 (dd, J = 3.6, 1.1 Hz, 1H), 7.27 (d, J = 8.2 Hz, 1H), 7.08 (dd,J = 5.1, 3.6 Hz, 1H), 6.98 (d, J = 2.1 Hz, 1H), 6.85 (dd, J = 8.2, 2.1 Hz,1H), 5.01 (s, 2H), 1.47 (s, 9H). ESI-MS m/z: 291.3 [M+H]+.
83% at 60℃; for 2 h; To a solution of tert-butyl (2-nitro-4-(thiophen-2-yl)phe- nyl)carbamate (1.6 g, 4.99 mmol, 1 eq.) in methanol (20 mE)was added hydrazine hydrate (14 mE) and ferric chloride (0.05 g, 0.3 mmol, 0.06 eq.). The resulting mixture was warmed to 60° C. and stirred for 2 h. The reaction was then filtered through Celite, the solids were washed with MeOH. The filtrate was concentrated under reduced pressure. Waterwas added to the residue and the suspension was stirred for 1 h. The obtained solid was filtered, washed with hexanes then dried to yield tert-butyl (2-amino-4-(thiophen-2-yl)phenyl) carbamate (1.2 g, 83percent yield).
69% With palladium 10% on activated carbon; hydrogen In methanol; ethanol for 12 h; To a solution of tert-butyl (2-nitro-4-(thiophen-2-yl)phe- nyl)carbamate (2 g, 6.2 mmol, 1.0 eq.) in ethanol (20 mE) andmethanol (20 mE) was added 10percent Pd/C (0.66 g, 0.1 eq.). The reaction mixture was stirred 12 h under a hydrogen atmosphere. The reaction was filtered and the filtrate was concen120trated under reduced pressure to give tert-butyl (2-amino-4- (thiophen-2-yl)phenyl)carbamate (1.25 g, 69percent yield) as an off-white solid.
54% With zinc In 1,4-dioxane; water at 70℃; Zinc powder (4.75 g) was added to a solution of 16 (6.65 g, 20.74 mmol) in dioxane (180 mL) and H2O (45 mL) and stirred overnight at 70 °C. Upon completion, EtOAc was added and the mixture was washed with H2O (3×100 mL) and brine (1×100 mL). The crude product was purified by column chromatography, eluting with EtOAc:Hexanes (2:1), to obtain 17 (3.95 g, 54 percent yield). 1H NMR (400MHz, CDCl3) δ 7.34–7.20 (m, 3H), 7.10–6.98 (m, 3H), 1.52 (s, 9H). 13C NMR (101MHz, CDCl3) δ 153.7, 144.1, 139.9, 132.2, 127.9, 124.8, 124.4, 122.8, 117.5, 115.0, 80.7, 28.3

Reference: [1] Patent: WO2014/160221, 2014, A1, . Location in patent: Page/Page column 49
[2] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 12, p. 2981 - 2994
[3] Patent: WO2007/118137, 2007, A1, . Location in patent: Page/Page column 83
[4] European Journal of Medicinal Chemistry, 2017, vol. 134, p. 185 - 206
[5] Patent: US9365498, 2016, B2, . Location in patent: Page/Page column 121
[6] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 4, p. 340 - 345
[7] Patent: US9365498, 2016, B2, . Location in patent: Page/Page column 120; 121
[8] European Journal of Medicinal Chemistry, 2015, vol. 96, p. 340 - 359
[9] Patent: US6509328, 2003, B1,
[10] Patent: US2007/117824, 2007, A1, . Location in patent: Page/Page column 28-29
[11] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 726 - 731
[12] Patent: WO2007/136605, 2007, A2, . Location in patent: Page/Page column 51
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Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 4, p. 340 - 345
[2] Patent: WO2014/160221, 2014, A1,
[3] Patent: US9365498, 2016, B2,
[4] European Journal of Medicinal Chemistry, 2017, vol. 134, p. 185 - 206
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 12, p. 2981 - 2994
[6] Patent: WO2007/136605, 2007, A2,
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  • [ 875-51-4 ]
  • [ 335255-43-1 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 4, p. 340 - 345
[2] Patent: WO2014/160221, 2014, A1,
[3] European Journal of Medicinal Chemistry, 2015, vol. 96, p. 340 - 359
[4] Patent: US9365498, 2016, B2,
[5] European Journal of Medicinal Chemistry, 2017, vol. 134, p. 185 - 206
[6] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 12, p. 2981 - 2994
  • 4
  • [ 24424-99-5 ]
  • [ 335255-43-1 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 4, p. 340 - 345
[2] Patent: WO2014/160221, 2014, A1,
[3] European Journal of Medicinal Chemistry, 2015, vol. 96, p. 340 - 359
[4] Patent: US9365498, 2016, B2,
[5] European Journal of Medicinal Chemistry, 2017, vol. 134, p. 185 - 206
[6] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 12, p. 2981 - 2994
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