2-Bromoethanol → HCID 58277361, compound

HRID 1949224Notes

Reaction equation

HRID 1949224 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+].Br[CH2:32][CH2:33][OH:34]>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][CH2:32][CH2:33][OH:34])[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 108982-BromoethanolHCID 11430Potassium CarbonateHCID 58277403HCID 58277403, compound

Product 1

HCID 58277361HCID 58277361, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

100 mg (0.29 mmol) of the compound of Example 44A are provided in 2 ml of dry acetone, 44.4 mg (0.32 mmol) of potassium carbonate and 36.5 mg (0.29 mmol) of 2-bromoethanol 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 13.1 mg 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 13.1 mg of the title compound
  5. customare obtained

Sources & evidence

ORD record
ord-7d9d1705d8e445d78b7d7d9fc7e3b1bf
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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