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

HRID 924294Notes

Reaction equation

HRID 924294 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.[CH:29]([C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:33]=1[N:39]1[C:43](=[O:44])[CH2:42][S:41]/[C:40]/1=[N:45]\[C:46](=O)[O:47]C1C=CC([N+]([O-])=O)=CC=1)([CH3:31])[CH3:30]>>[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:46](/[N:45]=[C:40]1\[S:41][CH2:42][C:43](=[O:44])[N:39]\1[C:33]1[CH:34]=[C:35]([CH3:38])[CH:36]=[CH:37][C:32]=1[CH:29]([CH3:30])[CH3:31])=[O:47])[CH:23]=[CH2:24]

Participants

3

Reactant 2

HCID 90412883N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)prop-2-en-1-amineHCID 117622068(4-nitrophenyl) (NZ)-N-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]carbamate

Product 1

HCID 90414028(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

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

  1. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-5f64ecdcb13543bab4c501debcf44aeb
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

Loading…