Cesium carbonate → (1Z)-1-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]-3-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]cyclohexyl]urea

HRID 1772535Notes

Reaction equation

HRID 1772535 reaction equation
[F:1][C:2]([F:29])([F:28])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]4[NH2:27])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[N+](C1C=CC([CH:39]2[S:43]/[C:42](=[N:44]\[C:45](=O)[O-:46])/[N:41]([C:48]3[CH:53]=[C:52]([CH3:54])[CH:51]=[CH:50][C:49]=3[CH:55]([CH3:57])[CH3:56])[C:40]2=[O:58])=CC=1)([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH:55]([C:49]1[CH:50]=[CH:51][C:52]([CH3:54])=[CH:53][C:48]=1[N:41]1[C:40](=[O:58])[CH2:39][S:43]/[C:42]/1=[N:44]\[C:45]([NH:27][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH:21]1[C:18]1[CH:19]=[CH:20][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:28])[F:29])=[CH:9][CH:8]=3)[N:11]=2)=[CH:16][CH:17]=1)=[O:46])([CH3:57])[CH3:56]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 904126112-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)cyclohexanamineHCID 178424959HCID 178424959, compound

Product 1

HCID 90412951(1Z)-1-[3-(5-methyl-2-propan-2-ylphenyl)-4-oxo-1,3-thiazolidin-2-ylidene]-3-[2-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]cyclohexyl]ureaYield 6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)cyclohexanamine (CB56) (0.200 g, 0.497 mmol) and (Z)-4-nitrophenyl(3-(2-isopropyl-5-methylphenyl)-4-oxothiazolidin-2-ylidene)carbamate (CA50) (0.205 g, 0.497 mmol) were dissolved in acetonitrile (10 mL) in a vial. Cesium carbonate (0.162 g, 0.497 mmol) was added, and the reaction was stirred at room temperature for 25 hours. The solution was adsorbed onto silica. Purification by reverse-phase flash column chromatography using 0-100% acetonitrile/water as eluent afforded the title compound as a red oil (0.020 g, 6%).

Workup

  1. customPurification by reverse-phase flash column chromatography

Sources & evidence

ORD record
ord-3cb3cc29c1ef4aea9a692eed969bd083
Source dataset
uspto-grants-2016_02
Patent number
US09249133B2

Reaction notes

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