N-methyl-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethanamine → (3Z)-1-methyl-3-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]-1-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]ethyl]urea

HRID 573935Notes

Reaction equation

HRID 573935 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[CH:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[N:12]=2)=[CH:7][CH:6]=1.[N+](C1C=CC([CH:36]2[S:40]/[C:39](=[N:41]\[C:42](=[O:44])[O-])/[N:38]([C:45]3[CH:50]=[C:49]([CH3:51])[CH:48]=[CH:47][C:46]=3[CH:52]([CH3:54])[CH3:53])[C:37]2=[O:55])=CC=1)([O-])=O>>[CH:52]([C:46]1[CH:47]=[CH:48][C:49]([CH3:51])=[CH:50][C:45]=1[N:38]1[C:37](=[O:55])[CH2:36][S:40]/[C:39]/1=[N:41]\[C:42](=[O:44])[N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]=[CH:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:24])([F:26])[F:25])=[CH:18][CH:17]=3)[N:12]=2)=[CH:7][CH:6]=1)([CH3:53])[CH3:54]

Participants

3

Reactant 2

HCID 90411907N-methyl-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethanamineHCID 178424959HCID 178424959, compound

Product 1

HCID 78319354(3Z)-1-methyl-3-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]-1-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]ethyl]urea

Procedure

The title compound was prepared as described in Example 95 using N-methyl-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethanamine (CB24) 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 pale orange foam (0.160 g, 63%).

Workup

  1. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-3d8fea345a0f4b31be7f6c8359aa5ec0
Source dataset
uspto-grants-2015_05
Patent number
US09029560B2

Reaction notes

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