Potassium Carbonate → N-Cyclopropyl-3-(2-(2-ethylbutyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide

HRID 907350Notes

Reaction equation

HRID 907350 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]([CH2:36][CH3:37])[CH2:34][CH3:35]>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]([CH2:36][CH3:37])[CH2:34][CH3:35])[CH:17]=[CH:16]4)[CH:7]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77432Pentane, 3-(bromomethyl)-HCID 25020457N-Cyclopropyl-4-methyl-3-(1-oxo-1,2-dihydro-isoquinolin-6-yl)-benzamide

Product 1

HCID 57551735N-Cyclopropyl-3-(2-(2-ethylbutyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the product of Example 11 (100 mg) in DMF (3 mL) was added potassium carbonate (217 mg) followed by 3-(bromomethyl)pentane (0.44 mL) and the mixture stirred at 80° C. for 17 hrs. The reaction mixture was filtered and purified by HPLC to give the title compound (55.0 mg) as a solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-48535875f14b4f9397e9755f43da321d
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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