3-(4-(3-(2,6-Difluorophenyl)ureido)-3-methylphenyl)isoxazole-5-carboxylic acid → 3-(4-(3-(2,4-Difluorophenyl)ureido)-3-methylphenyl)isoxazole-5-carboxylic acid
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:29])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[C:21]([C:23]([O:25]CC)=[O:24])[O:20][N:19]=2)=[CH:14][C:13]=1[CH3:28].FC1C=CC=C(F)C=1NC(=O)NC1C=CC(C2C=C(C(O)=O)ON=2)=CC=1C>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:29])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[C:21]([C:23]([OH:25])=[O:24])[O:20][N:19]=2)=[CH:14][C:13]=1[CH3:28]Participants
3
Procedure
The title compound was prepared using ethyl 3-(4-(3-(2,4-difluorophenyl)ureido)-3-methylphenyl)isoxazole-5-carboxylate following the same procedure as described for preparation of the compound of step 7 of Example 98. The title compound was obtained as a white solid (91%) after drying in vacuo; 1H NMR (300 MHz, DMSO-d6) δ: 2.30 (s, 3H), 7.01-7.06 (m, 1H), 7.27-7.34 (m, 1H), 7.66 (S, 1H), 7.71-7.74 (d, J=8.7 Hz, 1H), 7.78 (s, 1H), 8.08-8.17 (m, 2H), 8.48 (s, 1H), 9.11 (s, 1H); IR (KBr) 3289, 3076, 2926, 1709, 1651, 1594, 1557, 1502, 1426, 1285, 1230, 1142, 1100, 964, 851 cm−1.
Workup
- customThe title compound was prepared
Sources & evidence
- ORD record
- ord-d13471f641884217935e82d530bc3cf5
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835428B2
Reaction notes
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