2-(difluoromethyl)-1H-1,3-benzodiazole → HCID 22036898, compound

HRID 1789782Notes

Reaction equation

HRID 1789782 reaction equation
FC(F)C1NC2C=CC=CC=2N=1.FC(F)C1NC2C=C(O[Si](C(C)(C)C)(C)C)C=CC=2N=1.[F:33][CH:34]([F:70])[C:35]1[N:39]([C:40]2[N:45]=[C:44]([N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)[CH:43]=[C:42]([N:52]3[CH2:57][CH2:56][O:55][CH2:54][CH2:53]3)[N:41]=2)[C:38]2[CH:58]=[CH:59][C:60]([O:62][Si](C(C)(C)C)(C)C)=[CH:61][C:37]=2[N:36]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[F:70][CH:34]([F:33])[C:35]1[N:39]([C:40]2[N:41]=[C:42]([N:52]3[CH2:53][CH2:54][O:55][CH2:56][CH2:57]3)[CH:43]=[C:44]([N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)[N:45]=2)[C:38]2[CH:58]=[CH:59][C:60]([OH:62])=[CH:61][C:37]=2[N:36]=1

Participants

7

Reactant 4

HCID 5977032-(difluoromethyl)-1H-1,3-benzodiazoleHCID 2724141Tetrabutylammonium FluorideHCID 22036893HCID 22036893, compoundHCID 57420451HCID 57420451, compound

Product 1

HCID 22036898HCID 22036898, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In accordance with the procedure of the Example 1 except that 2-difluoromethylbenzimidazole in (1) of the Example 1 was replaced by 2-difluoromethyl-5-tert-butyldimethylsilyloxybenzimidazole, obtained was 2-(2-difluoromethyl-5-tert-butyldimethylsilyloxybenzimidazol-1-yl)-4,6-dimorpholinopyrimidine. 0.55 g (1.0 mmol) of the obtained compound dissolved in THF (10 ml) was added with a solution of tetrabutylammoniumfluoride (1 M) in THF (2 ml) and stirred at room temperature for 30 minutes. The reaction solution was poured into water and extracted with ethyl acetate. The separated organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography to obtain 0.40 g (yield: 93%) of the titled compound as colorless crystals.

Workup

  1. customobtained
  2. extractionextracted with ethyl acetate
  3. washThe separated organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1e6a466c51cc492e9ad3e90bd07420f0
Source dataset
uspto-grants-2006_07
Patent number
US07071189B2

Reaction notes

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