1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-{2-[5-(2H-tetrazol-5-yl)pyridin-3-yl]-1-benzothien-5-yl}urea
Reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:7]=[C:8]([C:12]2[S:16][C:15]3[CH:17]=[CH:18][C:19]([NH2:21])=[CH:20][C:14]=3[CH:13]=2)[CH:9]=[N:10][CH:11]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][C:24]=1[C:32]([F:35])([F:34])[F:33]>O1CCCC1.C(OCC)(=O)C>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH:21][C:19]2[CH:18]=[CH:17][C:15]3[S:16][C:12]([C:8]4[CH:9]=[N:10][CH:11]=[C:6]([C:5]5[N:1]=[N:2][NH:3][N:4]=5)[CH:7]=4)=[CH:13][C:14]=3[CH:20]=2)=[O:31])=[CH:25][C:24]=1[C:32]([F:33])([F:34])[F:35]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
The reaction mixture of 2-(5-(2H-tetrazol-5-yl)pyridin-3-yl)benzo[b]thiophen-5-amine (44.1 mg, 0.15 mmol, 1 eq) and 4-chloro-3-(trifluoromethyl)phenyl isocyanate (33.2 mg, 1 eq) in anhydrous tetrahydrofuran (1.5 mL) under nitrogen atmosphere was stirred at room temperature for 45 minutes. The reaction was then diluted with ethyl acetate, washed with aqueous ammonium chloride, brine, and dried with anhydrous sodium sulfate. The upper clear solution was decanted and concentrated. The soft solid was wrapped with silica gel and chromatographed (EtOAc to MeOH-EtOAc 1:4) to give 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-{2-[5-(2H-tetrazol-5-yl)pyridin-3-yl]-1-benzothien-5-yl}urea as a yellow powder in the amount of 26 mg.
Workup
- washwashed with aqueous ammonium chloride, brine
- dry with materialdried with anhydrous sodium sulfate
- customThe upper clear solution was decanted
- concentrationconcentrated
- customchromatographed (EtOAc to MeOH-EtOAc 1:4)
Sources & evidence
- ORD record
- ord-dd3cce632e8a4aa098a7e55f5a3e9433
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359336B2
Reaction notes
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