(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → 6-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-1H-benzoimidazole

HRID 1513224Notes

Reaction equation

HRID 1513224 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:14])[C:3]=1[C:15]1[NH:16][C:17]2[CH:23]=[C:22]([C:24]([NH:26][NH:27][C:28](=O)[C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)=[O:25])[CH:21]=[CH:20][C:18]=2[N:19]=1.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>C1COCC1.O.CCCCCCC>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([C:28]2[O:25][C:24]([C:22]3[CH:21]=[CH:20][C:18]4[N:19]=[C:15]([C:3]5[C:2]([CH3:1])=[CH:7][C:6]([N:8]6[CH2:13][CH2:12][O:11][CH2:10][CH2:9]6)=[CH:5][C:4]=5[CH3:14])[NH:16][C:17]=4[CH:23]=3)=[N:26][N:27]=2)=[CH:34][CH:33]=1

Participants

6

Reactant 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 669663874-Chloro-benzoic acid N'-[2-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-3H-benzoimidazole-5-carbonyl]-hydrazide

Product 1

HCID 252358566-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-1H-benzoimidazole

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

252 mg of 4-Chloro-benzoic acid N′-[2-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-3H-benzoimidazole-5-carbonyl]-hydrazide was placed in a microwave tube and dissolved in 4 ml of THF. 300 mg of (methoxycarbonylsulfamoyl)triethylammonium hydroxide (Burgess Reagent) was added and the tube was sealed and microwaved at 150° C. for 30 minutes. The reaction was then diluted with water and heptane. The precipitates were collected by filtration and purified by column chromatography (heptane:ethyl acetate=1:1 to 1:2) to provide the title compound. LCMS ret T=1.44 min, m/z=486.1, method 10. 1H NMR (400 MHz, MeOD) □ ppm 2.29 (br. s., 6 H) 3.36 (br. s., 5 H) 3.99 (br. s., 4 H) 6.95 (br. s., 2 H) 7.81 (s, 2 H) 7.95 (br. s., 1 H) 8.25 (br. s., 1 H) 8.32 (br. s., 2 H) 8.56 (br. s., 1 H).

Workup

  1. customthe tube was sealed
  2. custommicrowaved at 150° C. for 30 minutes
  3. filtrationThe precipitates were collected by filtration
  4. custompurified by column chromatography (heptane:ethyl acetate=1:1 to 1:2)

Sources & evidence

ORD record
ord-3d2842c89eda4d688810157110622cde
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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