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With triethylamine; In tetrahydrofuran; at 75℃; for 12h;
To l-benzyl-<strong>[4876-59-9]N,N-dimethylpiperidin-4-amine dihydrochloride</strong> (6.7 g, 23 mmol) was added Pd/C (10%, 2.4 g) under argon. Methanol (100 ml) was added via syringe, and H2 gas was introduced and the mixture stirred vigorously under an atmosphere of H2. After 48 h, the mixture was flushed with nitrogen, filtered through celite and concentrated to afford a mixture of starting material and <strong>[4876-59-9]N,N-dimethylpiperidin-4-amine dihydrochloride</strong> as a white solid. This solid was treated with l-Fluoro-2-nitro-4- trifluoromethyl-benzene (3.2 ml, 22.9 mmol), triethylamine (12.7 ml, 92 mmol), and 50 ml dry THF. The mixture was heated to 75 0C with a water-cooled reflux condenser for 12 h. The mixture was allowed to cool to ambient temperature, was filtered through a fritted funnel, and concentrated to an orange oil. The residue was purified by silica gel chromatography (MC/MeOH/cone. NH4OH) to give the desired product as an orange oil. MS (m/z) : 318.1 (M+H)+. Calc'd for C14H18F3N3O2: 317.31.
ethyl 2-(2-nitro-4-trifluoromethylanilino)benzo[b]thiophene-3-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
STARTING MATERIAL SYNTHESIS EXAMPLE 47 In the same manner as in Starting Material Synthesis Example 4 and using <strong>[7311-95-7]ethyl 2-aminobenzo[b]thiophene-3-carboxylate</strong> (5.0 g), 4-fluoro-3-nitrobenzotrifluoride (5.1 g) and dirnethyl sulfoxide (65 ml), ethyl 2-(2-nitro-4-trifluoromethylanilino)benzo[b]thiophene-3-carboxylate (12 g) was obtained.
(2S,3S)-3-Amino-2-methyl-7-(trifluoromethyl)-2,3-dihydrobenzo[b][l,4]oxazepin- 4(5H)-one trifluoroacetate In a similar manner to that described for the preparation of (S)-3-amino-8-methyl-2,3- dihydrobenzo[b][l,4]oxazepin-4(5H)-one trifluoroacetate except in Step 1 the mixture was stirred overnight and in Step 2 the mixture was stirred 3 h, (2S,3S)-2-(tert- butoxycarbonylamino)-3-hydroxybutanoic acid discyclohexylamine salt (2.0 g, 5.00 mmol) and l-fluoro-2-nitro-4-(trifluoromethyl)benzene (1.04 g, 5.00 mmol) were converted to the title compound (58 mg) which was used without purification.
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