Dibutyltin oxide → HCID 178461506, compound

HRID 2110151Notes

Reaction equation

HRID 2110151 reaction equation
FC(F)(F)OC1C=CC(N2CCNCC2)=CC=1.[CH3:18][C@H:19]1[CH2:24][N:23]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=2)[CH2:22][C@@H:21]([CH3:36])[N:20]1[S:37]([C:40]1[CH:48]=[CH:47][CH:46]=[C:45]2[C:41]=1[CH2:42][CH:43]([C:49]#[N:50])[CH2:44]2)(=[O:39])=[O:38].C([Sn](=O)CCCC)CCC.[N:61]([Si](C)(C)C)=[N+:62]=[N-:63]>C1(C)C=CC=CC=1>[CH3:18][C@H:19]1[CH2:24][N:23]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:33])([F:35])[F:34])=[CH:27][CH:26]=2)[CH2:22][C@@H:21]([CH3:36])[N:20]1[S:37]([C:40]1[C:41]2[CH2:42][CH:43]([C:49]3[NH:63][N:62]=[N:61][N:50]=3)[CH2:44][C:45]=2[CH:46]=[CH:47][CH:48]=1)(=[O:39])=[O:38]

Participants

6

Reactant 4

HCID 61221Dibutyltin oxide2×HCID 78378Azidotrimethylsilane2×HCID 230811701-(4-(Trifluoromethoxy)phenyl)piperazineHCID 575651884-[cis-2,6-Dimethyl-4-(4-trifluoromethoxy-phenyl)-piperazine-1-sulfonyl]-indan-2-carbonitrile

Product 1

HCID 178461506HCID 178461506, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

cis-2,6-Dimethyl-1-|2-(1H-tetrazol-5-yl)-indane-4-sulfonyl|-4-(4-trifluoromethoxy-phenyl)-piperazine: 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

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customdirectly purified by silica gel column chromatography (0-10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-aecb900843f9441eabe00b22860e91a5
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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