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derivative of benzamide | Bread Market Cafe

derivative of benzamide

derivative of benzamide

The catalyst was filtered off, the filtrate was evaporated in vacuo, and the resulting residue was dissolved in hydrochloric acid (2N; 100 ml) and then the solution was adjusted to pH 5 by treatment with concentrated aqueous ammonia solution. Rk represents a hydrogen atom, C₁₋₆ alkyl group, amino group, mono-C₁₋₆ alkylamino group, or di-C₁₋₆ alkylamino group, wherein the C₁₋₆ alkyl group may be substituted with 1 to 3 hydroxyl, amino, mono-C₁₋₆ alkylamino, and/or di-C₁₋₆ alkylamino groups; and 2,868,691 and 3,095,355. The inorganic base includes sodium hydroxide, lithium hydroxide, and potassium hydroxide, and is preferably sodium hydroxide. C-7 N-(5-Chloro-2-ethanesulfonyl-benzyl)-4-((R)-3-dimethylaminomethyl-piperidin-1-ylmethyl)-3-trifluoromethyl-benzamide Potassium trifluoro(methyl)borate (430 mg, 3.53 mmol), butyldi-1-adamanthylphosphine (63.3 mg, 0.176 mmol), potassium carbonate (731 mg, 5.29 mmol) and palladium(II) acetate (19.8 mg, 0.0880 mmol) were added to a mixed solution of ethyl 2-amino-3-bromo-4-formyl-5-(trifluoromethyl)benzoate (Compound e1, 600 mg, 1.76 mmol) in toluene (6.0 ml) and water (2.0 ml) at room temperature, and it was stirred at 90° C. for 15 hours. 2-Amino-5-trifluoromethyl-4-vinyl-benzoic acid ethyl ester 259°-260° C. (with decomposition); 5-cyano-2-hydroxy-N-(tetrazol-5-yl)benzamide, m.p. The conditions to be selected in this step such as the reaction reagent and the solvent are the same as those in Step I-8. The solution was sequentially washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, followed by drying over anhydrous sodium sulfate. N-20 HPLC retention time: 0.41 min (analysis condition F) [2-Ethylsulfanyl-5-(trifluoromethyl)phenyl]hydrazine Compound dd34 220° C. (a) Dry 2-benzyloxy-5-chlorobenzoic acid (1.15 g) was treated, with stirring, with dry pyridine (20 ml) and anhydrous 5-aminotetrazole (3.72 g). Compound P-4 However, under the Compound ee1 conditions, tert-butyl N-methyl-N-[(3S)-pyrrolidin-3-yl]carbamate was used in place of tert-butyl piperazine-1-carboxylate. HPLC retention time: 0.42 min (analysis condition F) Example 121 104 0.19 The compounds of the present invention are formulated by combining ingredients that are generally used as materials for pharmaceutical preparations, using conventional methods. 95°-96° C., and. The title compound was synthesized from {(R)-1-[2-bromo-4-(5-chloro-2-ethanesulfonyl-benzylcarbamoyl)-6-trifluoromethyl-benzyl]-piperidin-3-yl}-carbamic acid tert-butyl ester (Compound e8) under the same conditions as for Compound B-57. The compositions may also comprise, as is normal practice, additional substances other than inert diluents, e.g. Compound d7 LCMS: m/z 276 [M+H]⁺ K-15 After concentration under reduced pressure, the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to yield the title compound (650 mg, 71%). 0.78 As a further feature of the invention, compounds of the general formula: ##STR8## [wherein R8 represents a straight- or branched-chain alkyl group containing from 1 to 6 carbon atoms, r represents an integer 1, 2 or 3, R9 represents a fluorine, chlorine or bromine atom, or a straight- or branched-chain alkyl, alkoxy, alkylsulphonyl, alkanoylamino or alkylsulphamoyl group, each such group containing from 1 to 6 carbon atoms, a dialkylsulphamoyl or dialkylcarbamoyl group (wherein the two alkyl groups may be the same or different and each contains from 1 to 4 carbon atoms), a straight- or branched-chain alkanoyl, alkoxycarbonyl, alkoxycarbonylamino or alkylcarbamoyl group containing from 2 to 6 carbon atoms, or a nitro, trifluoromethyl, aryl (e.g. 353 G-3 LCMS: m/z 554 [M+H]⁺ Herein, “arylsulfonyl” refers to a sulfonyl group to which the above-defined “aryl” is bounded (i.e., aryl-SO₂—). 1H-NMR (400 MHz, CDCl₃) δ: 3.82-3.95 (2H, m), 3.66 (3H, s), 2.73-2.83 (1H, m), 2.44-2.54 (1H, m), 2.31-2.38 (2H, m), 1.76-1.86 (1H, m), 1.34-1.73 (5H, m), 1.45 (9H, s), 1.01-1.15 (1H, m). The title compound was synthesized from 4-((R)-3-amino-pyrrolidin-1-ylmethyl)-3-chloro-N-(5-chloro-2-ethanesulfonyl-benzyl)-5-trifluoromethyl-benzamide (Compound D-5) under the same conditions as for Compound B-9. 3-Chloro-N-(5-chloro-2-ethanesulfonyl-benzyl)-4-((R)-3-methanesulfonylamino-pyrrolidin-1-ylmethyl)-5-trifluoromethyl-benzamide (3.5 min) → 10/90 (1 HPLC retention time: 0.50 min (analysis condition A) The conditions to be selected in this step such as the reaction reagent and the solvent are the same as those in Step IV-6. 80 0.14 Example 714 However, 3-chloro-5-(trifluoromethyl)benzoic acid was used in place of 3-bromo-5-(trifluoromethyl)benzoic acid. The compound or compounds may also be administered orally by inhalation in the form of a dry micronised powder, which may be diluted with one or more suitable pharmaceutically acceptable inert solid diluents selected from, for example, lycopodium, boric acid, starch, bismuth subcarbonate and heavy magnesium carbonate. Example 220 Ethyl 3-chloro-4-[[3-[(2-methylpropan-2-yl)oxycarbonylamino]azetidin-1-yl]methyl]-5-(trifluoromethyl)benzoate Production Method II Example 282 The solvents were then removed in vacuo and the residue was recrystallized from water, with the aid of charcoal, to give 3-methylsulphonylsalicylic acid (1.5 g), m.p. 290°-292° C. (with decomposition). HPLC retention time: 0.89 min (analysis condition F) Step VI-7 Preferred examples of the solvent include aprotic polar solvents, ether solvents, and halomethane solvents. N-(5-Chloro-2-ethanesulfonyl-benzyl)-3-(3,3-dimethyl-piperazin-1-yl)-5-trifluoromethoxy-benzamide Compound c9 The title compound was synthesized from 4-(3-amino-2-chloro-4-ethoxycarbonyl-6-trifluoromethoxy-benzyl)-piperazine-1-carboxylic acid tert-butyl ester (Compound f5) under the same conditions as for Compound b31. 554 N-[(5-Chloro-2-ethylsulfonylphenyl)methyl]-4-hydroxy-3-(trifluoromethyl)benzamide 68 However, potassium hydroxide was used in place of sodium hydroxide under the conditions for Compound b8. Temp. However, the reaction was performed with the addition of copper iodide. N-(5-Bromo-2-ethanesulfonyl-benzyl)-3-trifluoromethyl-benzamide The title compound was synthesized from tert-butyl N-[(3S)-1-[[4-[(5-chloro-2-ethylsulfonylphenyl)methylcarbamoyl]-2-methyl-6-(trifluoromethyl)phenyl]methyl]piperidin-3-yl]-N-methylcarbamate (Compound k5) under the same conditions as for Compound B-57. This step can be performed by reacting the amide derivative V-q with a primary or secondary amine corresponding to Y1-Z1-Pro. 0.034 Example 580 R⁶ represents a hydrogen atom or a group represented by formula (i) below: 265°-267° C. (with decomposition) (recrystallized from acetic acid); 3-ethoxy-2-hydroxy-N-(tetrazol-5-yl)benzamide, m.p.

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