N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)prop-2-en-1-amine → (3Z)-3-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]-1-prop-2-enyl-1-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]ethyl]urea
Reaction equation
[F:1][C:2]([F:28])([F:27])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:26]=[CH:25][C:18]([CH2:19][CH2:20][NH:21][CH2:22][CH:23]=[CH2:24])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[N+](C1C=CC([CH:38]2[S:42]/[C:41](=[N:43]\[C:44](=O)[O-:45])/[N:40]([C:47]3[CH:52]=[C:51]([CH3:53])[CH:50]=[CH:49][C:48]=3[CH:54]([CH3:56])[CH3:55])[C:39]2=[O:57])=CC=1)([O-])=O>>[CH2:22]([N:21]([CH2:20][CH2:19][C:18]1[CH:25]=[CH:26][C:15]([C:12]2[N:13]=[CH:14][N:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:27])[F:28])=[CH:9][CH:8]=3)[N:11]=2)=[CH:16][CH:17]=1)[C:44](/[N:43]=[C:41]1\[S:42][CH2:38][C:39](=[O:57])[N:40]\1[C:47]1[CH:52]=[C:51]([CH3:53])[CH:50]=[CH:49][C:48]=1[CH:54]([CH3:55])[CH3:56])=[O:45])[CH:23]=[CH2:24]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared as described in Example 95 using N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)prop-2-en-1-amine (CB26) and (Z)-4-nitrophenyl(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate (CA50), purified by flash column chromatography using 0-100% ethyl acetate/B, where B=1:1 dichloromethane/hexanes, as eluent and isolated as a brown oil (0.040 g, 43%).
Workup
- custompurified by flash column chromatography
Sources & evidence
- ORD record
- ord-790ce5e052724d3ab206fb9f5fd2d57b
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249133B2
Reaction notes
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