HCID 68647887, compound → HCID 68648000, compound

HRID 1161757Notes

Reaction equation

ClC1C=CC(NC=C(C2ON=C(C)C=2)C(NC2C=CC(F)=CC=2)=O)=CC=1.C([O:29][C:30]1[CH:35]=[CH:34][C:33]([NH:36][CH:37]=[C:38]([C:49]2[O:53][N:52]=[C:51]([CH3:54])[CH:50]=2)[C:39]([NH:41][C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=2)=[O:40])=[CH:32][CH:31]=1)C.ClC1C=CC(NC(=O)C(=CNC2C=CC=C(F)C=2)C2ON=C(C)C=2)=CC=1>>[F:48][C:45]1[CH:46]=[CH:47][C:42]([NH:41][C:39](=[O:40])[C:38](=[CH:37][NH:36][C:33]2[CH:32]=[CH:31][C:30]([OH:29])=[CH:35][CH:34]=2)[C:49]2[O:53][N:52]=[C:51]([CH3:54])[CH:50]=2)=[CH:43][CH:44]=1

Participants

Reactant 3

HCID 68647887HCID 68647887, compound

HCID 68648135HCID 68648135, compound

HCID 68648186HCID 68648186, compound

Product 1

HCID 68648000HCID 68648000, compoundYield 40%

Procedure

Yield 40%. α-[[(4-Chlorophenyl)amino]methylene]-N-(4-fluorophenyl)-3-methyl-5-isoxazoleacetamide: Yield 44%, 1H NMR (400 MHz, CDCl3) δ 11.50 (d, 1H), 8.28 (s, 1H), 7.70 (d, 1H), 7.50 (d, 2H), 7.30 (d, 4H), 7.00 (d, 2H), 6.01, 6.20 (s, 1H), 2.30, 2.35 (s, 3H); TOF MS ES+ m/z 372, 374 (MH+); 394, 396 (M+Na+); α-[[(4-Ethoxyphenyl)amino]methylene]-N-(4-fluorophenyl)-3-methyl-5-isoxazoleacetamide: Yield 47%; 1H NMR (400 MHz, CDCl3) δ 11.40 (d, 1H, J=12.3 Hz), 8.26 (br s, 1H), 7.67 (d, 1H, J=12.9 Hz), 7.48 (d, 2H, J=9.1 Hz), 7.04 (d, 2H, J=8.9 Hz), 7.01 (d, 2H, J=8.9 Hz), 6.98 (d, 2H, J=8.9 Hz), 5.95 (s, 1H), 4.00 (q, 2H, J=6.9 Hz), 2.31 (s, 3H), 1.40 (t, 2H, J=6.9 Hz); N-(4-Chlorophenyl)-α-[(3-fluorophenylamino)methylene]-3-methyl-5-isoxazole-acetamide; Isolated in 44% yield. 1H NMR (400 MHz, CDCl3) δ 11.50 (d, 1H), 8.30, 8.15 (d, 1H), 7.70 (d, 1H), 7.50 (d, 2H), 7.30 (dd, 3H), 6.80 (m, 3H), 6.22, 6.02 (s, 1H), 2.35, 2.30 (s, 3H). TOF MS ES+ m/z 372, 374 (M+H+) 394, 396 (M+Na+).

Workup

customIsolated in 44% yield

Sources & evidence

ORD record: ord-f72653fe2dee48589a7fd27249c49e30
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820663B2

Reaction notes

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