Potassium Carbonate → HCID 23158544, compound

HRID 869338Notes

Reaction equation

HRID 869338 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][O:34][C:35]1[CH:44]=[CH:43][CH:42]=[CH:41][C:36]=1[C:37]([O:39][CH3:40])=[O:38]>CN(C)C=O>[NH2:24][C:15]1[N:14]=[C:13]([O:12][CH2:8][CH2:9][CH2:10][CH3:11])[N:21]=[C:20]2[C:16]=1[N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:32][CH2:33][O:34][C:35]1[CH:44]=[CH:43][CH:42]=[CH:41][C:36]=1[C:37]([O:39][CH3:40])=[O:38]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10491482HCID 10491482, compoundHCID 178450370HCID 178450370, compound

Product 1

HCID 23158544HCID 23158544, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound obtained in Example 2-1 step (v) was dissolved in dimethylformamide (50 ml), and potassium carbonate (3.52 g) and methyl 2-(2-bromoethoxy)benzoate (2.2 g) were added thereto. The mixture was stirred at room temperature for 96 hours and partitioned between ethyl acetate and 2M hydrochloric acid. The organic layer was dried and concentrated under reduced pressure. The residue was dissolved in methanol and purified by RPHPLC to give the titled compound. Yield: 0.768 g (22%).

Workup

  1. custompartitioned between ethyl acetate and 2M hydrochloric acid
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in methanol
  5. custompurified by RPHPLC

Sources & evidence

ORD record
ord-220b3572bab348cf80437570005cf59f
Source dataset
uspto-grants-2015_03
Patent number
US08969362B2

Reaction notes

Loading…