(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 1360727Notes

Reaction equation

HRID 1360727 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., 6H) 3.36 (br. s., 5H) 3.99 (br. s., 4H) 6.95 (br. s., 2H) 7.81 (s, 2H) 7.95 (br.s., 1H) 8.25 (br. s., 1H) 8.32 (br. s., 2H) 8.56 (br. s., 1H).

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-0e633de60ffd4e1da4a437e22bab6e32
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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