Potassium Carbonate → HCID 58277295, compound

HRID 1949227Notes

Reaction equation

HRID 1949227 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)=[CH:11][C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:31][O:32][CH2:33][CH2:34]Br>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:34][CH2:33][O:32][CH3:31])[CH:14]=3)=[CH:11][C:10]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 58277403HCID 58277403, compound

Product 1

HCID 58277295HCID 58277295, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

100 mg (0.292 mmol) of the compound of Example 44A are provided in 2 ml of dry acetone, 44.4 mg (0.321 mmol) of potassium carbonate and 40.6 mg (0.292 mmol) of 2-bromoethyl methyl ether are added, and the mixture is heated under reflux overnight. The reaction mixture is subsequently purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with the addition of 0.1% formic acid) and 48 mg (41% of theory) of the title compound are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. customThe reaction mixture is subsequently purified by preparative HPLC (RP18 column
  4. additionmobile phase: acetonitrile/water gradient with the addition of 0.1% formic acid) and 48 mg (41% of theory) of the title compound
  5. customare obtained

Sources & evidence

ORD record
ord-8d8ab397e78d43bf8f4cd1e167b9715f
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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