(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → N-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-2-yl)benzamide

HRID 714348Notes

Reaction equation

HRID 714348 reaction equation
[C:1]([NH:9][NH:10][C:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:14]=1)=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>O1CCCC1>[C:2]1([C:1]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20](=[O:27])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:14]=3)=[N:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 67153859N-(4-(2-benzoylhydrazinecarbonyl)pyridin-2-yl)benzamide

Product 1

HCID 67153787N-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-2-yl)benzamideYield 32.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-(2-benzoylhydrazinecarbonyl)pyridin-2-yl)benzamide (0.10 g, 0.27 mmol) in tetrahydrofuran (10 mL) was added (methoxycarbonylsulfamoyl)-triethylammonium hydroxide (0.35 g, 0.63 mmol) at ambient temperature. The resulting solution was refluxed for 7 hours and concentrated in vacuo to dryness. The residue was purified by column chromatography to give N-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-2-yl)benzamide (0.03 g 32%): mp 151-155° C.; 1H NMR (300 MHz, CDCl3) δ 9.03-9.00 (m, 2H), 8.41 (br s, 1H), 8.19-7.97 (m, 2H), 7.97-7.94 (m, 2H), 7.84-7.83 (m, 1H), 7.61-7.48 (m, 6H); 13C NMR (75 MHz, CDCl3) δ 168.1, 167.6, 164.9, 154.7, 151.1, 135.9, 135.4, 134.7, 134.3, 131.3, 131.1, 129.4, 127.3, 125.4, 119.0, 112.9; MS (ES+) m/z 343.5 (M+1).

Workup

  1. temperatureThe resulting solution was refluxed for 7 hours
  2. concentrationconcentrated in vacuo to dryness
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a14a6add85ef461ab4974a50ecf837b2
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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