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Chemical Structure| 7113-02-2

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Product Details of [ 7113-02-2 ]

CAS No. :7113-02-2
Formula : C11H9NO2S
M.W : 219.26
SMILES Code : O=C(C1=CSC(C2=CC=CC=C2)=N1)OC
MDL No. :MFCD06204179

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Application In Synthesis of [ 7113-02-2 ]

* 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.

  • Downstream synthetic route of [ 7113-02-2 ]

[ 7113-02-2 ] Synthesis Path-Downstream   1~10

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YieldReaction ConditionsOperation in experiment
80% With sodium hydroxide; In methanol; at 0℃; for 2h; General procedure: These compounds 4a-f were prepared using the general methoddescribed by Gududuru et al. [35]. Sodium hydroxide solution (1 M,2.5 mL) was added to a solution of (12a-f), 40-175 mg, in methanol(2.5 mL) at 0 C. The solution was stirred for 2 h, and then themethanol was evaporated in vacuo. The solutionwas acidified withconc HCl and extracted with EtOAc (3 50 mL). The combinedorganic layers were washed with water (50 mL) and brine (50 mL),then dried over Na2SO4, filtered and evaporated in vacuo to affordthe corresponding carboxylic acid derivatives 4a-f.
With sodium hydroxide; In methanol; at 0℃; for 2h; Example 3-Synthesis of Thiazole Carboxylic Acid Amides[0101] The synthesis of thiazole derivative (compound 34) was accomplished starting from cysteine as shown in scheme 3.[0102] To a solution of DL-cysteine (3g, 24.76 mmol) in MeOH (50 mL) at 0 C, SOCl2 (2.76 mL, 37.14 mmol) was slowly added and warmed to room temperature then refluxed for 3 h. The reaction mixture was concentrated in vacuo to yield a residue. This residue was taken in to aqueous EtOH (1: 1,30 mL), NaHCO3 (2.28 g, 27.23 mmol) was added, after 10 min benzaldehyde (2.5 mL, 24.76 mmol) was added and stirring continued for 3 h. CHC13 (200 mL) was added to the reaction mixture and washed with water, brine, dried (Na2S04) and solvent was removed in vacuo. The crude product was purified by column chromatography to afford 2- phenylthiazolidine-4-carboxylic acid methyl ester (compound 31): yield 4.7 g, 85%;lH NMR (CDCl3) 6 7.51-7. 62 (m, 2H), 7.32-7. 42 (m, 3H), 5.84 (s, 0.4H), 5.58 (s, 0.6H), 4.24 (t, J= 6.3 Hz, 0.4H), 4.01 (t, J= 7.5 Hz, 0.6H), 3.83 (s, 3H), 3.39-3. 55 (m, 1H), 3.10-3. 26 (m, 1H) ; MS (ESI)m/z 224 (M+1).[0103] Beginning with compound 31,2-phenylthiazole-4-carboxylic acid methyl ester (compound 32) was synthesized following a reported procedure (Kue et al. , "Essential Role for G Proteins in Prostate Cancer Cell Growth and Signaling," Urol. 164: 2162-2167 (2000), which is hereby incorporated by reference in itsentirety). Yield 0.33 g, 68% ; 1H NMR (CDCl3) # 8.20 (s, 1H), 8.0-8. 04 (m, 2H), 7.45-7. 50 (m, 3H), 4.0 (s, 3H); MS (ESI) m/z 220 (M+1).[0104] To a solution of compound 32 (0.5 g, 2.28 mmol) in MeOH (10 mL) at 0 C, IN NaOH (5 mL) was added and stirred for 2 h. To the reaction mixture EtOAc (30 mL) was added and acidified with IN HC1. Extracted with EtOAc (3X50 mL), combined extracts were washed with water, brine, dried (Na2SO4) and solvent was removed under vacuo to give crude acid (compound 33), which was converted to 2- phenylthiazole-4-carboxylic acid octadecylamide (compound 34) following the general procedure described in Example 1 above. Yield 0.30 g, 68%;1H NMR (CDCl3) 88. 10 (s, 1H), 7.96-7. 93 (m, 2H), 7.46-7. 50 (m, 3H), 3.49 (dd,J= 13. 5,6. 9 Hz, 2H), 1.69 (m,2H), 1.27(m, 30H), 0.89 (t, J= 6.3 Hz, 3H); MS(ESI) m/z calcd forC28H45N20S 457.73(M+1), obsd 457.60.
Add compound 3 (1 mmol) to a round bottom flask at room temperature, add 12 ml of a mixture of MeOH/THF/2.0 N NaOH (2:2:2) to dissolve it, and determine the reaction by TLC (developing agent V petroleum ether / After the end of V ethyl acetate = 2:1), 10 ml of water was added to the reaction system, pH was adjusted to 2 to 3 with 2N HCl, and extracted with EA (3×20 ml), dried over anhydrous sodium sulfate and dried. Get carboxylic acid 4. Compound 4 was used directly in the next reaction without further purification.
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  • 4
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  • methyl 5-(3-benzylamino-3-oxoprop-1-en-1-yl)-2-phenylthiazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With silver(I) acetate; palladium diacetate; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 115℃; for 48h; General procedure: A reaction tube was charged with methyl 4-phenylthiazole-4-carboxylate (1a, 0.5 mmol), olefin 2 (0.75 mmol, 1.5 equiv), Pd(OAc)2 (11 mg, 0.05 mmol, 10 mol%), AgOAc (167 mg, 1 mmol, 2.0 equiv), DMF (1.5 ml) and DMSO (0.15 ml). The mixture was vigorously stirred at 115 C (oil temperature). After stirring for 48 h, the mixture was cooled to room temperature, diluted with ethyl acetate and filtered. The filtrate was washed with saturated NaHCO3, water and brine, dried over Na2SO4, and concentrated in vacuo to give dark residue, which was purified by flash chromatography on silica gel to afford the cross coupling product 3a (155 mg, 90%) as off-white solid
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  • 10
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  • [ 13406-29-6 ]
  • [ 1315510-22-5 ]
  • [ 1427954-76-4 ]
YieldReaction ConditionsOperation in experiment
58%; 25% With silver(I) acetate; palladium diacetate; trifluoroacetic acid; In 1-methyl-pyrrolidin-2-one; at 120℃; for 48h;Inert atmosphere; Schlenk technique; General procedure: 4.3.27 methyl 2-phenyl-5-(4-trifluoromethylphenyl)thiazole-4-carboxylate (4g) A suspension of Pd(OAc)2 (10 mol percent), Ar3P (0.33 mmol or 0.75 mmol), AgOAc (3.0 mmol), TFA (1.0 mmol) and azole-4-carboxylates (0.5 mmol) in NMP (2 mL) was introduced to a Schlenk tube. After stirring at 120 C under argon for 24 h (reactions with 0.33 mmol of Ph3P), or 48 h (reactions with 0.75 mmol of Ph3P), the reaction mixture was diluted with ethyl acetate, and then filtered through a pad of Celite. Volatiles were removed in vacuo to give the crude products, which was purified by flash column chromatography on silica gel to afford pure arylated products Yield 45 mg (25percent). White solid, mp 147-149 °C; 1H NMR (300 MHz, CDCl3) delta 3.88 (s, 3H), 7.47-7.49 (m, 5H), 7.66-7.73 (m, 4H), 7.97-8.00 (m, 2H) ppm; 13C NMR (75 MHz, CDCl3) delta 165.9, 161.3, 143.2, 133.0, 131.4, 130.4, 129.9, 129.3, 129.1, 128.0, 125.8, 124.2, 124.1, 121.0, 51.3 ppm; IR (KBr) 2950, 2838, 1714, 1610, 1506, 1217, 1181, 1094, 835, 786, 708, 683 cm-1; HRMS (ESI) calcd for [C18H12F3NO2S+H]+ 364.0614, found 364.0615.
 

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