Dichloromethane → HCID 22503472, compound

HRID 1251096Notes

Reaction equation

HRID 1251096 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH2:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[C:20]([C:28]3[CH:33]=[CH:32][C:31]([CH:34](O)[CH2:35][CH3:36])=[CH:30][CH:29]=3)[N:19]=2)[CH2:14][CH2:13]1)[CH3:11].C(=O)(O)[O-].[Na+].C(OCC)(=O)C.C(Cl)[Cl:50]>>[ClH:50].[CH2:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[C:20]([C:28]3[CH:33]=[CH:32][C:31]([CH:34]([F:7])[CH2:35][CH3:36])=[CH:30][CH:29]=3)[N:19]=2)[CH2:14][CH2:13]1)[CH3:11]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 9907659HCID 9907659, compound

Product 1

HCID 22503472HCID 22503472, compound

Procedure

Diethylaminosulfur trifluoride (0.27 g) was added to a solution of 1-(4-ethylpiperazin-1-yl)-3-[4-(1-hydroxypropyl)phenyl]isoquinoline (0.53 g) obtained in Example 19 in methylene chloride (30 ml) at −78° C. After stirring the resulting mixture for 1 hr, it was returned to room temperature. An aqueous solution of saturated sodium bicarbonate and ethyl acetate were added to the resulting reaction solution, for partitioning. The resulting organic layer was washed with water and brine, dried and concentrated. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system) (0.38 g), and was then converted into a hydrochloride in a conventional manner, to give 0.36 g of the title compound as a yellow powder.

Workup

  1. customwas returned to room temperature
  2. customfor partitioning
  3. washThe resulting organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system) (0.38 g)

Sources & evidence

ORD record
ord-88f93f77f1e74e528cf66174e1ccd8cf
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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