Potassium Carbonate → HCID 68766494, compound

HRID 2391689Notes

Reaction equation

HRID 2391689 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([N:7]2[C:15]3[CH:14]=[C:13]([C:16](=[O:22])[NH:17][CH2:18][CH2:19][O:20][CH3:21])[N:12]=[CH:11][C:10]=3[N:9]=[CH:8]2)[S:4][C:3]=1[C:23]([O:25][CH3:26])=[O:24].C([O-])([O-])=O.[K+].[K+].Br[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]([F:44])([F:43])[F:42]>CN(C)C=O>[CH3:21][O:20][CH2:19][CH2:18][NH:17][C:16]([C:13]1[N:12]=[CH:11][C:10]2[N:9]=[CH:8][N:7]([C:5]3[S:4][C:3]([C:23]([O:25][CH3:26])=[O:24])=[C:2]([O:1][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[C:41]([F:42])([F:43])[F:44])[CH:6]=3)[C:15]=2[CH:14]=1)=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 68766230HCID 68766230, compound2×

Product 1

HCID 68766494HCID 68766494, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.5 g of methyl 3-hydroxy-5-{6-[(2-methoxyethyl)carbamoyl]-1H-imidazo[4,5-c]pyridin-1-yl}thiophene-2-carboxylate (compound C5) in 10 ml anhydrous N,N-dimethylformamide were added 610 mg K2CO3 and 1.14 g 1-(bromomethyl)-2-(trifluoromethyl)benzene under a nitrogen atmosphere. The reaction mixture was stirred for 12 h at room temperature, poured into 400 ml of ice water and the resulting precipitate was filtered. The filter cake was washed with water, dissolved in 300 ml ethyl acetate and washed with 50 ml saturated aqueous KCl solution. The organic layer was separated, dried with MgSO4 and concentrated under vacuum. The residue was crystallized from methanol to yield the title compound.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washThe filter cake was washed with water
  3. dissolutiondissolved in 300 ml ethyl acetate
  4. washwashed with 50 ml saturated aqueous KCl solution
  5. customThe organic layer was separated
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated under vacuum
  8. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-33fd1ca1cd164ee3aabc2d71a13f9311
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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