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Structure of 25026-34-0
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 25026-34-0 |
Formula : | C8H6Cl2O |
M.W : | 189.04 |
SMILES Code : | O=C(Cl)CC1=CC=C(Cl)C=C1 |
MDL No. : | MFCD00037111 |
InChI Key : | UMQUIRYNOVNYPA-UHFFFAOYSA-N |
Pubchem ID : | 90692 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H312-H314-H332 |
Precautionary Statements: | P260-P261-P264-P270-P271-P280-P301+P312-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P312-P321-P322-P330-P363-P405-P501 |
Class: | 8 |
UN#: | 3265 |
Packing Group: | Ⅱ |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of <strong>[17672-21-8]methyl 2-amino-3-hydroxybenzoate</strong> (2 g) and methylene chloride (40 mL) was ice-cooled, and added triethylamine (3.34 mL) and 4-chlorophenylacetylchloride (1.93 mL) in this order, followed by stirring at the same temperature for 2 hours and at room temperature overnight. To the reaction mixture were added water (50 mL) and chloroform (50 mL), and the separated organic layer was washed with 1 M hydrochloric acid, a saturated sodium bicarbonate solution, and saturated saline in this order, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was dissolved in toluene (40 mL), and p-toluene sulfonic acid (2.47 g) was added thereto, followed by heating under reflux for 4 hours. After leaving it to be cooled, dilution with ethyl acetate (80 mL) was carried out, followed by washing with 1 M hydrochloric acid, a saturated sodium bicarbonate solution, and saturated saline in this order. The precipitated solid was removed by filtration, and then the filtrate was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=3:1) to obtain methyl 2-(4-chlorobenzyl)-1,3-benzoxazole-4-carboxylate (850 mg) as a pale yellow syrup. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | at 150℃; for 0.0833333h;Microwave irradiation; | General procedure: Amide formation: (0088) The acid chloride (1 eq) formed on the corresponding 2-aminobenzothiazole (1 eq) is added introduced in a microwave vial. The vial is introduced in the microwave reactor and heated to the temperature for the time indicated in each case. Dichloromethane (50 mL) is added and extracted with a 0.1 M HCl (50 mL) solution. Next, the organic phase is washed with saturated NaHC03 solution (50 mL) and then with saturated NaCl (50 mL) solution. The organic phase is dried over anhydrous MgS04 and the solvent removed under reduced pressure. The residue obtained was purified by flash column chromatography using Isolera One equipment. In all cases a mixture of hexane and ethyl acetate was used as eluent. All the acid chlorides required for the synthesis of the amide derivatives were synthesised in situ except: 2-(4-chlorophenyl)acetyl chloride, 2-(2,5-dimethoxyphenyl)acetyl chloride and 2-phenylbutanoyl chloride, which were purchased directly from the company Sigma Aldrich. N-(6-trifluoromethylbenzothiazole-2-yl)-2-(4-chlorophenyl)acetamide (1): Reagents: 2-(4-chlorophenyl)acetyl chloride (216.7 mg, 1.1 mmol) and 2-amino-6-trifluoromethylbenzothiazole (250 mg, 1.14 mmol). Reaction conditions: 5 min under microwave irradiation at 150°C. Purification by flash column chromatography using hexane/ethyl acetate (3:1) to obtain a white solid. Yield: 404.1 mg, 95percent. Mp: 135°C-137°C 1H NMR (300 MHz, DMSO-d6) delta: 12.84 (s, 1 H), 8.48 (s, 1 H), 7.90 (d, J = 8.5 Hz, 1 H), 7.73 (d, J = 8.4 Hz, 1 H), 7.49 - 7.27 (m, 4H), 3.87 (s, 2H). 13C NMR (75 MHz, DMSO-d6) delta: 170.4, 161.1, 151.2, 134.0, 133.4, 132.0, 131.3, 128.1, 124.5 (d, J = 272.0 Hz), 123.7 (d, J = 31.8 Hz), 122.9 (d, J = 3.9 Hz), 120.9, 1 19.9 (d, J = 4.3 Hz) 41.0. HPLC purity: >99percent. ESI-MS (m/z): 371 [M+H]+. Elemental analysis (C16H10ClF3N2OS): Theoretical percentC 51.83, percentH 2.72, percentN 7.56, percentS 8.64; Found percentC 52.00, percentH 2.71, percentN 7.55, percentS 8.49. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Methyi 3-amino-4-fluorobenzoate (88 mg, 0.530 mmoi) and 4-chiorophenyiacetyi chioride (77 jii, 0.520 mmoi) in toiuene (6 mi) were heated at 100 °C for 1 h. Lawesson reagent (210 mg, 0.520 mmoi) was added and the mixture was heated at 110 °C overnight. Soivent wasevaporated and residue purified by flash chromatography using 20percent EtOAc in hexanes aseiuent. Yieid: 72.4 mg (44percent); white soiid. MS(ESI+) m/z 318 [M+H]. HPLC purity: 100percentPEPPSI-iPr?M (ca 5 mg) was added to a mixture of the chioride from above (54.4 mg, 0.17 1 mmoi), 4-pyridineboronic acid (25.2 mg, 0.205 mmoi) and potassium carbonate (35.5 mg, 0.256 mmoi) in toiuene (2 mi) and MeOH (2 mi). The mixture was heated at 100 °C for 45mm in a microwave reactor. Water and EtOAc were added. The aqueous iayer was extracted with EtOAc and combined organic iayer evaporated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In dichloromethane; at 20℃; for 2.0h; | General procedure: To a stirred solution of <strong>[56293-29-9]aloperine</strong> (2.0 mmol) and K2CO3(6.0 mmol) in anhydrous CH2Cl2, a solution of 6 in anhydrousCH2Cl2 was added dropwise. The reaction mixture was stirred for2 h till TLC analysis showed completion of the reaction. Then thesolution was washed with water (20 ml) and brine (20 mL), driedover anhydrous sodium sulfate and then evaporated under reducedpressure to get the crude 7 which was applied directly in the nextstep without further purification. |
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