Dibutyltin oxide → HCID 178461506, compound
Reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)[CH2:5][C@@H:4]([CH3:19])[N:3]1[S:20]([C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH2:25][CH:26]([C:32]#[N:33])[CH2:27]2)(=[O:22])=[O:21].C([Sn](=O)CCCC)CCC.[N:44]([Si](C)(C)C)=[N+:45]=[N-:46]>C1(C)C=CC=CC=1>[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:16])([F:18])[F:17])=[CH:10][CH:9]=2)[CH2:5][C@@H:4]([CH3:19])[N:3]1[S:20]([C:23]1[C:24]2[CH2:25][CH:26]([C:32]3[NH:46][N:45]=[N:44][N:33]=3)[CH2:27][C:28]=2[CH:29]=[CH:30][CH:31]=1)(=[O:22])=[O:21]Participants
Conditions
- Temperature
- 105 °C
Procedure
To a solution of 4-[cis-2,6-dimethyl-4-(4-trifluoromethoxy-phenyl)-piperazine-1-sulfonyl]-indan-2-carbonitrile (23 mg, 0.0440 mmol) in toluene (1 ml) was added dibutyltin oxide (13 mg, 0.0281 mmol) and azidotrimethylsilane (5 μL, 0.0377 mmol). The reaction mixture was stirred at 105° C. for 20 h upon which an additional amount of dibutyltin oxide (13 mg, 0.0281 mmol) and azidotrimethylsilane (25 μL, 0.1884 mmol) was added and stirred at 105° C. for 4 h. The reaction mixture was cooled to room temperature and then directly purified by silica gel column chromatography (0-10% MeOH in dichloromethane) to afford cis-2,6-dimethyl-1-[2-(1H-tetrazol-5-yl)-indane-4-sulfonyl]-4-(4-trifluoromethoxy-phenyl)-piperazine (14 mg, 61%). 1H NMR (400 MHz, CD3OD) δ ppm 7.75 (d, 1H), 7.54 (d, 1H), 7.39 (t, 1H), 7.09 (d, 2H), 6.90 (d, 2H), 4.18-4.02 (m, 3H), 3.89 (dd, 1H), 3.59-3.51 (m, 2H), 3.36-3.31 (m, 3H), 2.66-2.60 (m, 2H), 1.48 (d, 6H). LCMS: 523.11 (M+1)+.
Workup
- additionwas added
- temperatureThe reaction mixture was cooled to room temperature
- customdirectly purified by silica gel column chromatography (0-10% MeOH in dichloromethane)
Sources & evidence
- ORD record
- ord-978b6c2e0d414caca79f2fdecb1dd2d5
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07494999B2
Reaction notes
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