Water → HCID 10384136, compound

HRID 1796321Notes

Reaction equation

HRID 1796321 reaction equation
Cl.[Br:2][C:3]1[N:4]=[C:5]([CH2:11]Cl)[N:6]([CH2:9][CH3:10])[C:7]=1[CH3:8].C([O-])([O-])=O.[K+].[K+].[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[NH:27][CH:28]=[CH:29][N:30]=2)[N:21]=1.O>CN(C=O)C>[Br:2][C:3]1[N:4]=[C:5]([CH2:11][N:30]2[CH:29]=[CH:28][N:27]=[C:26]2[C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([F:19])[N:21]=2)[N:6]([CH2:9][CH3:10])[C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridineHCID 22181651HCID 22181651, compound

Product 1

HCID 10384136HCID 10384136, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 77 mg (0.27 mmol) of 4-bromo-2-chloromethyl-1-ethyl-5-methyl-1H-imidazole hydrochloride in 1.5 ml of DMF is added 224 mg (1.62 mmol) of K2CO3 and 45 mg (0.27 mmol) of 2-fluoro-6-(1H-imidazol-2-yl)-pyridine. The mixture is stirred at room temperature for 24 hours. 5 ml water is added and the mixture was extracted with EtOAc (3×15 ml). The combined extracts are washed with 15 ml brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue is purified by preparative TLC, developing with 10:0.4:0.05 CH2Cl2—MeOH—NH4OH solution. The purified compound is then dissolved in 3 ml of EtOAc and to it is added 2 ml of 2N HCl in ether. The resulting suspension is stirred at room temperature for 15 minutes. Evaporation of the solvent 5 provides the title compound as a white powder. LC-MS (M+1) 364.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×15 ml)
  2. washThe combined extracts are washed with 15 ml brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue is purified by preparative TLC
  7. dissolutionThe purified compound is then dissolved in 3 ml of EtOAc and to it
  8. additionis added 2 ml of 2N HCl in ether
  9. stirringThe resulting suspension is stirred at room temperature for 15 minutes
  10. customEvaporation of the solvent 5

Sources & evidence

ORD record
ord-c10ae8d74a3949a7a6e085e08076f543
Source dataset
uspto-grants-2006_04
Patent number
US07030144B2

Reaction notes

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