2-(difluoromethyl)-1H-1,3-benzodiazole → HCID 66669741, compound

HRID 1789781Notes

Reaction equation

HRID 1789781 reaction equation
FC(F)C1NC2C=CC=CC=2N=1.FC(F)C1NC2C(O[SiH3])=C(C(C)(C)C)C(C)=C(C)C=2N=1.[F:33][CH:34]([F:72])[C:35]1[N:39]([C:40]2[N:45]=[C:44]([N:46]3[CH2:51][CH2:50][O:49][C@@H:48]([CH3:52])[C@H:47]3[CH3:53])[N:43]=[C:42]([N:54]3[CH2:59][CH2:58][O:57][CH2:56][CH2:55]3)[N:41]=2)[C:38]2[CH:60]=[CH:61][C:62]([O:64][Si](C(C)(C)C)(C)C)=[CH:63][C:37]=2[N:36]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[F:72][CH:34]([F:33])[C:35]1[N:39]([C:40]2[N:45]=[C:44]([N:46]3[CH2:51][CH2:50][O:49][C@@H:48]([CH3:52])[C@H:47]3[CH3:53])[N:43]=[C:42]([N:54]3[CH2:59][CH2:58][O:57][CH2:56][CH2:55]3)[N:41]=2)[C:38]2[CH:60]=[CH:61][C:62]([OH:64])=[CH:63][C:37]=2[N:36]=1

Participants

7

Reactant 4

HCID 5977032-(difluoromethyl)-1H-1,3-benzodiazoleHCID 2724141Tetrabutylammonium FluorideHCID 131725825HCID 131725825, compoundHCID 178425025HCID 178425025, compound

Product 1

HCID 66669741HCID 66669741, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In accordance with the procedure of the Example 4 except that 2-difluoromethylbenzimidazole in (1) of the Example 4 was replaced by 2-difluoromethyl-5-tert-butyldimethyl-silyloxybenzimidazole, obtained was 2-(2-difluoromethyl-5-tert-butyldimethylsilyloxybenzimidazol-1-yl)-4-(cis-2,3-dimethylmorpholino)-6-morpholino-1,3,5-triazine. 120 mg (0.22 mmol) of the obtained compound dissolved in THF (2 ml) was added with a solution of tetrabutylammoniumfluoride (1 M) in THF (0.5 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 75 mg (yield: 79%) 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-d9ba8b48dcf744dfb37d5d925a99469d
Source dataset
uspto-grants-2006_07
Patent number
US07071189B2

Reaction notes

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