2-Methyl-3-butyn-2-ol → (+/-)-9-Fluoro-3-(hydroxy(4-methylthiazol-5-yl)methyl)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

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9-fluoro-3-(hydroxy(4-methylthiazol-5-yl)methyl)-10-(3-hydroxy-3-methylbut-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was prepared similarly according to General Procedure G with slight modifications. 10-bromo-9-fluoro-3-[hydroxy-(4-methylthiazol-5-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide was reacted with 3-methyl-1-butyne-3-ol to afford 5.4 mg of the titled compound (18% yield). M+1=457.1. 1H NMR (400 MHz, DMSO) δ 8.87 (s, 1H), 8.58 (d, J=8.3 Hz, 1H), 8.01 (br s, 1H), 7.59-7.53 (m, 2H), 7.00 (d, J=10.5 Hz, 1H), 6.94 (d, J=6.3 Hz, 1H), 5.54 (s, 1H), 4.57-4.48 (m, 1H), 4.48-4.36 (m, 2H), 4.31-4.22 (m, 1H), 2.25 (s, 3H), 1.49 (s, 6H).

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