Cesium carbonate → HCID 66868822, compound

HRID 250775Notes

Reaction equation

HRID 250775 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([O:9][CH2:10]Cl)[CH3:8].[CH2:12]([N:16]1[C:20]2[CH:21]=[C:22]([C:25]3[C:26]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[N:27][NH:28][N:29]=3)[CH:23]=[CH:24][C:19]=2[N:18]=[C:17]1[NH2:36])[CH:13]([CH3:15])[CH3:14].[Cl-].[NH4+]>CN(C=O)C>[CH2:7]([O:9][CH2:10][N:28]1[NH:29][C:25]([C:22]2[CH:23]=[CH:24][C:19]3[N:18]=[C:17]([NH2:36])[N:16]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:20]=3[CH:21]=2)=[C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH:27]1)[CH3:8]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 18523Chloromethyl ethyl etherHCID 25517Ammonium ChlorideHCID 66868844HCID 66868844, compound

Product 1

HCID 66868822HCID 66868822, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add cesium carbonate (408 mg, 1.25 mmol) and chloromethyl ethyl ether (0.057 ml, 0.62 mmol) to a solution of 1-isobutyl-2-amino-6-(4-phenyl-2H-[1,2,3]triazol-5-yl)-1H-benzimidazole (208 mg, 0.62 mmol) in DMF (5 tri). Stir for 2 hours at RT, add aqueous ammonium chloride solution (20 ml) and extract with diethyl ether (20 ml). Dry over magnesium sulfate, concentrate and purify (radial silica gel chromatography, eluting with hexane:ethyl acetate 1:1) to provide the title compound as a white solid (32 mg, 13%).

Workup

  1. extractionextract with diethyl ether (20 ml)
  2. dry with materialDry over magnesium sulfate
  3. concentrationconcentrate
  4. custompurify
  5. wash(radial silica gel chromatography, eluting with hexane:ethyl acetate 1:1)

Sources & evidence

ORD record
ord-4ae4cfaa10ba4648b528b31810d0b993
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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