Potassium Carbonate → HCID 57551784, compound

HRID 907349Notes

Reaction equation

HRID 907349 reaction equation
[CH:1]1([NH:4][C:5](=[O:24])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[NH:18][CH:17]=[CH:16]4)[CH:7]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH:33]1[CH2:35][CH2:34]1>CN(C=O)C>[CH:1]1([NH:4][C:5](=[O:24])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:32][CH:33]3[CH2:35][CH2:34]3)[CH:17]=[CH:16]4)[CH:7]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503Bromomethylcyclopropane2×HCID 25020457N-Cyclopropyl-4-methyl-3-(1-oxo-1,2-dihydro-isoquinolin-6-yl)-benzamide

Product 1

HCID 57551784HCID 57551784, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of the product of Example 11 (100 mg), potassium carbonate (174 mg) and (bromomethyl)cyclopropane (63 mg) in DMF (2 mL) was stirred at room temperature for 16 hours and at 70° C. for 24 hours. Further (bromomethyl)cyclopropane (300 mg) was added and the mixture heated at 70° C. for a further 24 hours. The reaction mixture was filtered and purified by HPLC to give the title compound (70 mg) as a solid.

Workup

  1. temperaturethe mixture heated at 70° C. for a further 24 hours
  2. filtrationThe reaction mixture was filtered
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-ad8bdc2592034656ac10ab9efb8e255f
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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