Reaction Steps
Following the procedure as described in EXAMPLE 2.28 and making non-critical variations using 1′-[(5-chloro-1-methyl-1H-imidazol-2-yl)methyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one to replace 1-methyl-1′-{[5-(trifluoromethyl)furan-2-yl]methyl}-2,3-dihydro-1H-spiro[furo[3,2-g][1,4]benzoxazine-8,3′-indol]-2′(1′H)-one, 1′-[(5-chloro-1-methyl-1H-imidazol-2-yl)methyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one hydrochloride was obtained (82%) as a colorless solid: 207-208° C. (hexanes); 1H NMR (300 MHz, DMSO-d6) δ7.80 (s, 1H), 7.40 (d, J=7.8 Hz, 1H), 7.31 (dd, J=7.8, 7.2 Hz, 1H), 7.18 (d, J=7.2 Hz, 1H), 7.08 (dd, J=7.5, 7.2 Hz, 1H), 6.50 (s, 1H), 6.42 (s, 1H), 5.30 (s, 2H), 4.83 (d, J=9.6 Hz, 1H), 4.66 (d, J=9.6 Hz, 1H), 4.20-4.15 (m, 2H), 4.13-4.08 (m, 2H), 3.70 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ177.0, 154.8, 144.2, 141.8, 141.7, 137.9, 132.1, 128.6, 123.6, 123.5, 121.0, 120.9, 118.0, 111.9, 109.8, 98.6, 79.9, 64.2, 63.6, 57.3, 35.8, 31.9; MS (ES+) m/z 426.2 (M+1), 424.2 (M+1); Anal. Calcd for C22H18ClN3O4HCl.H2O: C, 55.24; H, 4.43; N, 8.78. Found: C, 55.51; H, 4.18; N, 8.58.
