1'-(diphenylmethyl)-1-methyl-1H-spiro[furo[3,2-g][1,4]benzoxazine-8,3'-indole]-2,2' (1'H,3H)-dione → 1-methyl-1H-spiro[furo[3,2-g][1,4]benzoxazine-8,3'-indole]-2,2'(1'H,3H)-dione
Reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3([C:30]4[C:19](=[CH:20][C:21]5[O:26][CH2:25][C:24](=[O:27])[N:23]([CH3:28])[C:22]=5[CH:29]=4)[O:18][CH2:17]3)[C:9]2=[O:31])C=CC=CC=1.C1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C3(C4C=C(C)C(OC)=CC=4OC3)C2=O)C=CC=CC=1>>[CH3:28][N:23]1[C:22]2[CH:29]=[C:30]3[C:10]4([C:11]5[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=5)[NH:8][C:9]4=[O:31])[CH2:17][O:18][C:19]3=[CH:20][C:21]=2[O:26][CH2:25][C:24]1=[O:27]Participants
Reactant 2
Product 1
Procedure
Following the procedure as described in EXAMPLE 3 and making non-critical variations using 1′-(diphenylmethyl)-1-methyl-1H-spiro[furo[3,2-g][1,4]benzoxazine-8,3′-indole]-2,2′(1′H,3H)-dione to replace 1′-(diphenylmethyl)-6-methoxy-5-methylspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one, 1-methyl-1H-spiro[furo[3,2-g][1,4]benzoxazine-8,3′-indole]-2,2′(1′H,3H)-dione was obtained (73%) as a colorless solid: mp>250° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 10.62 (br s, 1H), 7.29-7.22 (m, 1H), 7.11 (d, J=7.1 Hz, 1H), 7.02-6.90 (m, 2H), 6.70 (s, 1H), 6.48 (s, 1H), 4.80 (d, J=9.2 Hz, 1H), 4.66 (d, J=9.2 Hz, 1H), 4.58 (s, 2H), 3.07 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ178.1, 163.3, 156.7, 146.2, 141.9, 132.3, 128.9, 124.0, 123.9, 122.9, 122.3, 109.9, 99.1, 80.3, 67.1, 57.7, 28.0; MS (ES+) m/z 322.9 (M+1).
Sources & evidence
- ORD record
- ord-aa0d2e54f21148f1b6251aa3e9110ba9
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415370B2
Reaction notes
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