4(5H)-Thiazolone, 2-amino- → 4-[2-Fluoro-4-[(2-imino-4-oxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]naphthalene-1-carbonitrile
Reaction equation
[NH2:1][C:2]1[S:3][CH2:4][C:5](=[O:7])[N:6]=1.[F:8][C:9]1[CH:27]=[C:26]([CH:28]=O)[CH:25]=[CH:24][C:10]=1[O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]#[N:23])=[CH:14][CH:13]=1>>[F:8][C:9]1[CH:27]=[C:26]([CH:28]=[C:4]2[S:3][C:2](=[NH:1])[NH:6][C:5]2=[O:7])[CH:25]=[CH:24][C:10]=1[O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]#[N:23])=[CH:14][CH:13]=1Participants
3
Procedure
4-[2-Fluoro-4-(2-imino-4-oxo-thiazolidin-5-ylidenemethyl)-phenoxy]-naphthalene-1-carbonitrile was prepared using 2-amino-thiazol-4-one and 4-(2-Fluoro-4-formyl-phenoxy)-naphthalene-1-carbonitrile following General Procedure C. 1H NMR (400 MHz, DMSO-d6) δ 9.54 (br, 1H), 9.25 (br, 1H), 8.42 (d, J=8.21 Hz, 1H), 8.15 (d, J=8.21 Hz, 1H), 8.08 (d, J=7.82 Hz, 1H), 7.91 (m, 1H), 7.81 (m, 1H), 7.7 (dd, J=12.13 and 2.34 Hz, 1H), 7.64 (s, 1H), 7.49-7.57 (2H), 6.93 (d, J=7.83 Hz, 1H). LC/MS (m/z) [M+1]+390.2 (calculated for C21H13FN3O2S 390.1).
Sources & evidence
- ORD record
- ord-5e7b6bd506cb4c87a1da682dbf2c631d
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580832B2
Reaction notes
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