Sodium hydride → 1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-3-(4-(trifluoromethyl)pyridin-3-yl)thiourea

HRID 62056Notes

Reaction equation

HRID 62056 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[NH2:9].[H-].[Na+].[N:14]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:27]=[CH:26][N:25]([C:28]3[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=3)[N:24]=2)=[CH:19][CH:18]=1)=[C:15]=[S:16]>O1CCCC1>[F:38][C:35]([F:36])([F:37])[O:34][C:31]1[CH:30]=[CH:29][C:28]([N:25]2[CH:26]=[N:27][C:23]([C:20]3[CH:21]=[CH:22][C:17]([NH:14][C:15]([NH:9][C:4]4[CH:5]=[N:6][CH:7]=[CH:8][C:3]=4[C:2]([F:1])([F:10])[F:11])=[S:16])=[CH:18][CH:19]=3)=[N:24]2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27359573-Amino-4-(trifluoromethyl)pyridineHCID 1185901653-(4-Isothiocyanatophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

Product 1

HCID 1186750411-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)-3-(4-(trifluoromethyl)pyridin-3-yl)thioureaYield 16.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(trifluoromethyl)pyridin-3-amine (0.091 g, 0.56 mmol) in tetrahydrofuran and under an atmosphere of nitrogen was added sodium hydride (60% in mineral oil, 0.022 g, 0.56 mmol). 3-(4-Isothiocyanatophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (WO 2011/017513) (0.10 g, 0.28 mmol) was added and the reaction was allowed to stir for 48 hours. The reaction mixture was concentrated. Purification by silica gel chromatography provided the title compound (0.024 g, 16%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-b1a73d56817a4498959dac5c8bccb847
Source dataset
uspto-grants-2016_09
Patent number
US09445594B2

Reaction notes

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