Water → 5,6-Dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole-3-acetonitrile

HRID 617631Notes

Reaction equation

HRID 617631 reaction equation
Cl[CH2:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]([CH2:16][C:17]2[N:18]=[CH:19][N:20]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:21]=2)[N:4]=1.[O-][C:42]#[N:43].[K+].C(OCC)(=O)C.CCCCCC.O>CS(C)=O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]([CH2:16][C:17]1[N:18]=[CH:19][N:20]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:21]=1)[N:4]=[C:3]2[CH2:2][C:42]#[N:43]

Participants

6

Reactant 4

HCID 962WaterHCID 11378442Potassium cyanateHCID 154286393-Chloromethyl-5,6-dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazoleHCID 21226206Ethyl acetate hexane

Product 1

HCID 154286405,6-Dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole-3-acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-Chloromethyl-5,6-dimethoxy-1-(1-trityl-4-imidazolyl)methyl-1H-indazole (165.0 g) was suspended in dimethyl sulfoxide (1,200 ml) and stirred at room temperature. To this was added potassium cyanate (43.6 g) which has been made into powder using a mortar. When the reaction solution was stirred at 70° C. for 1 hour, the reaction solution became uniform and transparent, and it was observed that the spot of the material almost disappeared on a thin layer chromatography (ethyl acetate/hexane=2/1). The reaction solution was cooled to room temperature and poured into water (15,000 ml) which was vigorously stirred, and the mixture was stirred for 1 hour. The thus precipitated solid substance was collected by suction filtration, washed with water (1,000 ml×3) and dissolved in chloroform (5,000 ml), the resulting solution was dried with sodium sulfate and filtered, and then the solvent was evaporated under a reduced pressure. The thus obtained residue was separated and purified by a silica gel column (ethyl acetate) to obtain 108.7 g of light brown solid. This solid substance was directly used in the subsequent reaction.

Workup

  1. stirringWhen the reaction solution was stirred at 70° C. for 1 hour
  2. temperatureThe reaction solution was cooled to room temperature
  3. stirringwas vigorously stirred
  4. stirringthe mixture was stirred for 1 hour
  5. filtrationThe thus precipitated solid substance was collected by suction filtration
  6. washwashed with water (1,000 ml×3)
  7. dissolutiondissolved in chloroform (5,000 ml)
  8. dry with materialthe resulting solution was dried with sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated under a reduced pressure
  11. customThe thus obtained residue was separated
  12. custompurified by a silica gel column (ethyl acetate)
  13. customto obtain 108.7 g of light brown solid
  14. customThis solid substance was directly used in the subsequent reaction

Sources & evidence

ORD record
ord-7ea5b36cbfa843c5b6a0fbef7a02f845
Source dataset
uspto-grants-1999_09
Patent number
US05948913

Reaction notes

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