1-Bromo-3-chloropropane → HCID 58277401, compound

HRID 1949226Notes

Reaction equation

HRID 1949226 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][CH2:34][Cl:35]>CN(C=O)C>[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][CH2:34][Cl:35])[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 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 58277403HCID 58277403, compound

Product 1

HCID 58277401HCID 58277401, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.292 mmol) of the compound of Example 44A are provided in 3 ml of dry DMF, 76.6 mg (0.554 mmol) of potassium carbonate and 133 mg (0.846 mmol) of 1-bromo-3-chloropropane are added, and the mixture is heated under reflux for 4 h. 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 42 mg of the title compound with 49% purity (17% of theory) are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 4 h
  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 42 mg of the title compound with 49% purity (17% of theory)
  5. customare obtained

Sources & evidence

ORD record
ord-2c29b19634c74f5c96004a8441aad49f
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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