N-(cyclopropylmethyl)-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3 yl)phenyl)ethanamine → (3Z)-1-(cyclopropylmethyl)-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 924295Notes

Reaction equation

HRID 924295 reaction equation
[CH:1]1([CH2:4][NH:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:18]=[CH:17][N:16]([C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=4)[N:15]=3)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[CH:30]([C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][C:34]=1[N:40]1[C:44](=[O:45])[CH2:43][S:42]/[C:41]/1=[N:46]\[C:47](=O)[O:48]C1C=CC([N+]([O-])=O)=CC=1)([CH3:32])[CH3:31]>>[CH:1]1([CH2:4][N:5]([CH2:6][CH2:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:18]=[CH:17][N:16]([C:19]4[CH:20]=[CH:21][C:22]([O:25][C:26]([F:27])([F:28])[F:29])=[CH:23][CH:24]=4)[N:15]=3)=[CH:12][CH:13]=2)[C:47](/[N:46]=[C:41]2\[S:42][CH2:43][C:44](=[O:45])[N:40]\2[C:34]2[CH:35]=[C:36]([CH3:39])[CH:37]=[CH:38][C:33]=2[CH:30]([CH3:31])[CH3:32])=[O:48])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 90412446N-(cyclopropylmethyl)-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3 yl)phenyl)ethanamineHCID 117622068(4-nitrophenyl) (NZ)-N-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]carbamate

Product 1

HCID 90413008(3Z)-1-(cyclopropylmethyl)-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-(cyclopropylmethyl)-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethanamine (CB27) 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 red-orange oil (0.127 g, 60%).

Workup

  1. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-ba63d810ac9c4f3d987c8a5a32656518
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

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