Phenylindoles for the treatment of HIV
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b) 3-Arylsulfonylindole-2-carboxyamides—5a-g (Scheme 2, Examples 47)
[0441] The reaction of ethyl indole-2-carboxylates 2a-i with N-(3,5-dimethylphenylthio)-succinimide in the presence of sodium hydride afforded the ethyl 3-(3,5-dimethylphenylthio)indole-2-carboxylates 3a-i which were oxidized to the related sulfones 4a-i by treatment with 3-chloroperoxybenzoic acid. Transformation of esters 3a-i into related amides 4a-i was reached by heating in a sealed tube with ammonium hydroxide.
c) 3-Arylsulthioindole-2-carboxyhydrazides—6a-d, f and 7a-f—and 3-arylsulfonylindole-2-carboxyhydrazides—8a, b, d-f, 9a-f, 10 and 11 (Schemes 3 and 4, Examples 8-10)
[0442] Treatment of ethyl 3-aryllthioindole-2-carboxylates or 3-arylsulfonylindole-2-carboxylates with proper hydrazines afforded 3-arylsulthioindole-2-arboxyhydrazides (6a-d, f and 7a-f) and 3-arylsulfonylindole-2-arboxyhydrazides (8a, b, d-f and 9a-f, 10), respectively. Reaction of 7e with acetone in the presence of sodium cyanoborohydr...
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g) 5-(1H-Pyrrol-1-yl)-3-(3,5-dimethylphenylsulfonyl)indole-2-carboxyamide—25b (Scheme 8, Example 23)
[0446] 5-Nitro-3-(3,5-dimethylphenylsulfonyl)indole-2-carboxyamide (5k) was reduced 5-amino-3-(3,5-dimethylphenylsulfonyl)indole-2-carboxyamide with hydrogen in the presence of PtO2 (Adams' catalyst) as a catalyst. Transformation into 5-(1H-pyrrol-1-yl)-3-(3,5-dimethyl-phenylsulfonyl)indole-2-carboxylate (25a) was performed by heating with 2,5-dimethoxy-tetrahydrofuran in glacial acetic acid (Acta Chem. Scand., 1952, 6, 667-670; Acta Chem. Scand, 1952, 6, 867-874).
[0447] The following working examples provide a further understanding of the method of the present invention. These examples are of illustrative purpose, and are not meant to limit the scope of the invention. Equivalent, similar, or suitable solvents, reagents or reaction conditions may be substituted for those particular solvents, reagents or reaction conditions described herein without departing from the general scope o...
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Example 1
Synthesis of Ethyl Pyruvate 4-Chloro-3-Fluorophenylhydrazone
[0449] A solution of sodium nitrite (4.76 g, 0.069 mol) in water (6.3 mL) was added dropwise to an ice cooled mixture of 4-chloro-3-fluoroaniline (J. Am. Chem. Soc., 1996, 61, 5130-5133) (10.00 g, 0.069 mol), water (167 mL) and 37% hydrochloric acid (167 mL). After 20 minutes potassium acetate (9.81 g, 0.10 mol) was added, and then a solution of ethyl 2-methylacetoacetate (9.95 g, 0.069 mol), potassium acetate (9.81 g, 0.10 mol) in methanol (67 mL) was dropped while cooling on the ice bad. Reaction was stirred at 0° C. for 3 hours, then extracted with diethyl ether. Organic layer was washed with brine and dried. Removal of the solvent furnished a red oily residue that was treated with ethanol (100 mL) and stirred at room temperature overnight. The solid which formed was filtered a recrystallized from ethanol to give 5.4 g (30%) of title compound, mp 161-163° C. (from ethanol). [0450] Ethyl pyruvate 2,4-difluoroph...
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