Dibutyltin oxide → HCID 59275639, compound

HRID 1671870Notes

Reaction equation

HRID 1671870 reaction equation
N([Si](C)(C)C)=[N+:2]=[N-:3].[CH2:8]([Sn](=O)CCCC)CCC.[C:18]([C:20]1[C:24]2[CH:25]=[C:26]([O:34][CH:35]([CH3:37])[CH3:36])[C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][C:23]=2[O:22][C:21]=1[C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)#[N:19]>O1CCOCC1>[F:44][C:41]1[CH:40]=[CH:39][C:38]([C:21]2[O:22][C:23]3[CH:28]=[C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[C:26]([O:34][CH:35]([CH3:37])[CH3:36])=[CH:25][C:24]=3[C:20]=2[C:18]2[NH:3][N:2]=[CH:8][N:19]=2)=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 59275416HCID 59275416, compound

Product 1

HCID 59275639HCID 59275639, compoundYield 107.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Azidotrimethylsilane (34.2 μL, 0.257 mmol) was added to a stirring solution of dibutyltin oxide (6.41 mg, 0.026 mmol) and N-(3-cyano-2-(4-fluorophenyl)-5-isopropoxybenzofuran-6-yl)methanesulfonamide (50 mg, 0.129 mmol) in dioxane (1.3 mL) at rt. It was subjected to microwave irradiation for 15 min at 150° C. It was treated with additional equivalents of reagents and re-subjected for 30 min followed by 60 min. The mixture was concentrated and purified by preparative reverse phase HPLC on a C18 column using a suitably buffered gradient, and concentrated to give the titled compound (12 mg, 22%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.29-1.39 (m, 6H) 3.01 (s, 3H) 4.62-4.81 (m, 1H) 7.28-7.45 (m, 3H) 7.65 (s, 1H) 7.84-7.98 (m, 2H) 8.92 (s, 1H). LC-MS retention time: 1.04 min; m/z (MH+): 432. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters XBridge 5u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 2 min, a hold time of 1 min, and an analysis time of 3 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode. Additional HPLC method: Solvent A=5% CH3CN/95% H2O/0.1% TFA, Solvent B=95% CH3CN/5% H2O/0.1% TFA, Start % B=10, Final % B=100, Gradient time=15 min, Stop time=18 min, Flow Rate=1 ml/min. Column: Waters Sunfire C-18, 4.6×150 mm, 3.5 μm, Rt=11.56 min, purity=94%; Column: Waters Xbridge Phenyl column 4.6×150 mm, 3.5 μm, Rt=10.55 min, purity=96%.

Workup

  1. customirradiation for 15 min at 150° C
  2. additionIt was treated with additional equivalents of reagents
  3. waitfollowed by 60 min
  4. concentrationThe mixture was concentrated
  5. custompurified by preparative reverse phase HPLC on a C18 column
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3b2e21092703420ca17145821d32ad0e
Source dataset
uspto-grants-2011_08
Patent number
US07994171B2

Reaction notes

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