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1 Synthetic chemistry ML5 and ML4 were identified as K P.(TREK-) activators using a combination of fluorescence-based thallium flux and automated patch-clamp assays. ML5, ML4, and ML5a were synthesized using chemical synthesis procedures outlined below. ML5 was also purchased from Chembridge. Scheme : Synthesis of ML5 Step : Preparation of N-[(,4-dichlorophenyl)methyl]-4-methanesulfonamidobenzamide (ML5) A 5 ml reaction bottle equipped with a magnetic stirbar was charged with,4-dichlorobenzylamine ( µl, mmol, equiv.), 4-(methanesulfonylamino)benzoic acid (6 g, mmol, equiv.) and N,N-dimethylformamide (. ml). To the mixture was added HATU (4 g,. mmol,.5 equiv.) followed by triethylamine ( ml,. mmol,. equiv.) The reaction mixture was stirred for hours at room temperature and then partitioned between ethyl acetate and % aqueous citric acid. The organic layer was separated and washed with brine, then dried over Na S 4, decanted, and concentrated. The crude residue was re-suspended in dichloromethane and purified by automated silica gel flash chromatography on a g silica gel cartridge, using gradient elution with -% of ethyl acetate in hexane. Pure fractions were collected and concentrated to afford 44 mg of the desired product N-[(,4-dichlorophenyl)methyl]-4-methanesulfonamidobenzamide (6. % yield). H NMR ( MHz, DMS-d6) δ ppm.7 (s, H) 4.49 (d, J=5.46 Hz, H) 7.6 (m, J=8.67 Hz, H) 7.4 (d, J=8.67 Hz, H) 7.4 (d, J=8. Hz, H) 7.6 (s, H) 7.89 (m, J=8.48 Hz, H) 8.99 (br. s., H) 5 (s, H) C NMR (75 MHz, DMS-d6) δ ppm 9.68, 44, 8., 7., 8.57, 8.66, 8.8,.,.7,.88, 5.7, 4.46,65.89 LCMS predicted: m/z: m/z: 7. (.%), 74. (69.%), 7. (7.9%), 76. (.%), 75. (.8%), 77. (.%), 76. (.5%), 74. (.%) seen: [M+H] + (major) 7., 74.9 also [M+CH CN+H] + (major) 4.9,
2 Scheme : Synthesis of ML4 Step : Preparation of -[-(4-chloro--methylphenoxy)ethyl]-,-dihydro-H-isoindole-,- dione The preparation of this known compound was based on that described. A solution of diethyl azodicarboxylate (.58 ml, 7.8 mmol,.5 equiv.) in dry THF (5 ml) was added under dry nitrogen to a solution of -(4-chlorophenoxy) ethylamine ( g, 5. mmol, equiv.), triphenylphosphine (.6 g, 7.8 mmol,.5 equiv.) and 4-chloro--methylphenol (.9 g, 7.8 mmol,.5 equiv.) in dry THF (5 ml). The reaction mixture was stirred at room temperature overnight then concentrated. The residue was re-suspended in diethyl ether and the solid filtered off on Celite. The filtrate was concentrated and the residue was re-dissolved in dichloromethane and then purified by silica gel chromatography on an 8 g silica gel cartridge using gradient elution with -% ethyl acetate in hexane to afford g of the desired product - [- (4-chloro--methylphenoxy)ethyl] -,-dihydro-h isoindole-,-dione (56 % yield). Step : Preparation of -(-aminoethoxy)-4-chloro--methylbenzene Deprotection of the amine function was accomplished according to the procedure described in. A 5 ml reaction bottle with a magnetic stir bar was charged with -[-(4-chloro--methylphenoxy)ethyl],-dihydro-H-isoindole-,-dione (47 mg,. mmol, equiv.) and methanol ( ml) was added, followed by hydrazine monohydrate (5 µl, mmol, 7.8 equiv.). The reaction mixture was stirred for 7 hours at room temperature after which time the reaction was judged complete. The solvent was evaporated chloroform was added, the organic layer was washed with water and brine and then dried over Na S 4, decanted, and concentrated. The residue was re-suspended in dichloromethane and applied purified by silica gel chromatography on a g silica gel cartridge using gradient elution -% of % NH 4 H in methanol in dichloromethane to afford 79 mg of the desired product ( aminoethoxy) 4 chloro methylbenzene ( % yield).
3 H NMR ( MHz, CHLRFRM-d) δ ppm.9 (s, H).9 (t,j=4.9 Hz, H).4 (s, H).95 (t, J=5.9 Hz, H) 6.7 (d, J=8.9 Hz, H) (m, H) C NMR (75 MHz, CHLRFRM-d) δ ppm 6.45, 4.8, 79,.9, 5.5, 6.7, 8.94, 6, 55.8 LCMS (done on crude reaction mixture), predicted: m/z: 85.6 (.%), 87.6 (.%), 86.6 (%), 88.6 (.%) seen: [M+H] + (major) = 86., also [M+CH CN+H] + 7., 9. Step : Preparation of N-[-(4-chloro--methylphenoxy)ethyl]thiophene--carboxamide (ML4) A 5 ml reaction bottle with a magnetic stirbar was charged with ( aminoethoxy) 4 chloro methylbenzene (9 mg, mmol, equiv.), thiophene--carboxylic acid (7 mg, mmol, equiv.) and N,N-dimethylformamide (. ml, 5.9 mmol,.4 equiv.). To the mixture was added added HATU ( mg, mmol,.5 equiv.) followed by triethylamine (89 µl, mmol,. equiv.) The reaction mixture was stirred for hours at room temperature and then partitioned between ethyl acetate and % aqueous citric acid. The organic layer was separated and washed with brine, then dried over Na S 4, decanted, and concentrated. The residue was re-suspended in dichloromethane and purified by automated silica gel flash chromatography on a g silica gel cartridge, using gradient elution with -% of ethyl acetate in hexane. The resulting residue (8.5mg) was further purified by preparative HPLC (C8 column, 4% to 9% methanol in water,.5% formic acid) to afford mg of the desired product N-[-(4-chloro--methylphenoxy)ethyl]thiophene--carboxamide (9 % yield). H NMR ( MHz, CHLRFRM-d) δ ppm.4 (s, H).89 (q, J=5.7 Hz, H) 4.4 (t, J=5.5 Hz, H) 6.48 (br. s., H) 6.76 (d, J=8. Hz, H) (m, H) 7.5 (d, J=5.9 Hz, H) 7.54 (d, J=.58 Hz, H) C NMR (75 MHz, CHLRFRM-d) δ ppm 6.8, 9.9, 67.8,., 5.66, 6.5, 7.69, 8.5, 8.49,.6, 4, 8.45, 55.8, 6.95 LCMS predicted: m/z: 95.4 (.%), 97.4 (6.5%), 96.5 (5.4%), 98.4 (5.9%), 99.4 (.7%), 97.5 (.6%), 96.4 (.%) seen: [M+H] + (major) 96., 98.
4 Scheme : Synthesis of ML5a Step : Preparation of trans tert butyl N-(4-{[(,4- dichlorophenyl)methyl]carbamoyl}cyclohexyl)carbamate A round bottom flask was charged with Boc-trans-,4-aminocyclohexane carboxylic acid (8 mg, mmol, equiv.) and N,N-dimethylformamide (5 ml). To the mixture was added added HATU (44 mg,. mmol,.5 equiv.) followed by,4-dichlorobenzylamine ( µl, mmol, equiv.), and finally triethylamine ( ml,. mmol,. equiv.). The reaction mixture was stirred for an hour at room temperature and then diluted with ethyl acetate and % aqueous citric acid. The organic layer was separated and washed with brine, leading to the formation of a precipitate. The entire two-phase mixture was therefore filtered and the precipitate collected on a paper filter. This afforded the product, trans tert butyl N-(4-{[(,4-dichlorophenyl)methyl]carbamoyl}cyclohexyl)carbamate (57 mg, mmol, 86%), which was used in the next step without further purification. H NMR ( MHz, CHLRFRM-d) δ ppm. (dd, J=.87,.9 Hz, H).44 (s, 8 H).57 (dd, J=.4,. Hz, H).9 (d, J=.8 Hz, H) (m, H) 4.47 (d, J=6. Hz, H) 5.9 (br. s., H) 7. (dd, J=8.9,.98 Hz, H) 7. (d, J=8.9 Hz, H) 7.8 (d, J=.7 Hz, H) LCMS: predicted: m/z: 4 (.%), 4. (64.%), 4.4 (%), 4 (.7%), 44. (%), 4.4 (.7%), 45. (.%), 44.4 (.%) Seen: (only fragment, m-5 observed (major): 86., 88. Step : Preparation of trans-4-amino-n-[(,4-dichlorophenyl)methyl]cyclohexane-- carboxamide hydrochloride A 5 ml round-bottom flask was charged with trans tert butyl N (4 {[(,4 dichlorophenyl)methyl]carbamoyl}cyclohexyl)carbamate (57 mg, mmol) dissolved in dichloromethane (4. ml) with stirring, and then treated with a hydrochloric acid solution (4. ml of 4M 4
5 solution in,4 dioxane, 6. mmol, 5. equiv.). The reaction mixture was stirred overnight and then the solvent was evaporated to afford crude trans-4 amino N [(,4 dichlorophenyl)methyl]cyclohexane carboxamide hydrochloride (44 mg, mmol), which was used in the next step without further purification. H NMR ( MHz, DMS-d6) δ ppm (m, 4 H).8 (d, J=.6 Hz, H). (d, J=9.6 Hz, H).9 (m., H).95 (br. s., H) 4.7 (d, J=5.7 Hz, H) 7. (d, J=8.9 Hz, H) 7.4 (d, J=8.85 Hz, H) 7.6 (s, H) 8.5 (br. s., H) 8.46 (t, J=5.5 Hz, H) LCMS, predicted: m/z:.8 (.%),.8 (64.%), 8 (5.9%), 4.7 (%),.8 (9.8%), 5.8 (.6%),.9 (.%) seen: [M+H] + (major) = 9,.9 Step : Preparation of trans-n-[(,4-dichlorophenyl)methyl]-4-ethenesulfonamidocyclohexane- -carboxamide A 5 ml round bottom flask was charged with trans-4 amino N [(,4 dichlorophenyl)methyl]cyclohexane carboxamide hydrochloride (5 mg, mmol,. equiv.) dissolved in dichloromethane (.5 ml). The mixture was stirred in an ice bath and treated with triethylamine (.8 ml, mmol, 5. equiv.), followed by methanesulfonyl chloride (9 µl, mmol, equiv.). The reaction mixture was stirred for hours while warming to room temperature. During the reaction a precipitate formed, and this was collected by vacuum filtration on a paper filter. The solid was saved and the filtrate was applied directly on a g silica gel cartridge and purified using gradient elution (-% ethyl acetate in hexanes). Relevant fractions were collected and concentrated to afford 9.5 mg of the product, which was identical to the precipitate collected directly from the reaction mixture. Combined, this amounted to 9 mg of the desired product, trans-n-[(,4-dichlorophenyl)methyl]-4-ethenesulfonamidocyclohexane--carboxamide ( mmol, 9% over two steps). H NMR ( MHz, DMS-d6) δ ppm. (m, H).4 (m H).76 (d, J=6 Hz, H).9 (d, J=9. Hz, H).-. (m, H).89 (s, H) (m, H) 4.5 (d, J=5.84 Hz, H) 6.98 (d, J=7.54 Hz, H) 7.6 (d, J=8. Hz, H) 7.4 (dd, J=8.8,.7Hz, H) 7.59 (d, J=.7 Hz, H) 8.9 (t, J=5.5 Hz, H) C NMR ( MHz, DMS-d6) δ ppm 8.9,.9, 9.8, 4, 4.7, 5.49, 7., 8.5, 9.9,.8,.89, 5.77, 74.9 LCMS: Predicted: m/z: 78.6 (.%), 8.5 (68.4%), 79.6 (7.4%), 8.5 (.%), 86 (.5%), 8.5 (.%), 8.6 (.%), 8.6 (.4%), 85 (%), observed (m/z): [M+H] + = (major) 79.,
6 References. Pascale, R. et al. New N-(phenoxydecyl)phthalimide derivatives displaying potent inhibition activity towards alpha-glucosidase. Bioorg Med Chem 8, , doi:6/j.bmc ().. Eguchi, Y., Sasaki, F., Sugimoto, A., Ebisawa, H. & Ishikawa, M. Studies on Hypotensive Agents - Synthesis of -Substituted -(-Chlorophenyl)-6-Ethoxycarbonyl-5,7-Dimethyl-,4(h,h)- Quinazolinediones. Chem Pharm Bull 9, (99). 6
7 ML5- H NH 5 9 S CH 5 NH ML5- C
8 ML5- C solvent region NH 5 9 S CH NH ML5- C aryl region
9 5 5 ML4- H 7 S 6 5 NH CH ML4- C
10 ML4- C alkyl region 7 S NH CH ML4- C aryl region
11 ML5a- H S 8 NH NH ML5a- C
12 ML5a- C alkyl region 9 S 8 NH NH ML5a- C aryl region
All solvents and reagents were used as obtained. 1H NMR spectra were recorded with a Varian
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