Potassium Carbonate → N-Cyclopropyl-4-methyl-3-(1-oxo-2-(4-(pyrrolidin-1-ylmethyl)benzyl)-1,2-dihydroisoquinolin-6-yl)benzamide

HRID 907263Notes

Reaction equation

HRID 907263 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([NH:10][C:11](=[O:30])[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[C:25](=[O:29])[NH:24][CH:23]=[CH:22]4)[CH:13]=2)[CH2:9][CH2:8]1.Cl[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39]Cl)=[CH:35][CH:34]=1.[NH:41]1[CH2:45][CH2:44][CH2:43][CH2:42]1>CN(C=O)C>[CH:7]1([NH:10][C:11](=[O:30])[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[C:25](=[O:29])[N:24]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([CH2:39][N:41]5[CH2:45][CH2:44][CH2:43][CH2:42]5)=[CH:35][CH:34]=3)[CH:23]=[CH:22]4)[CH:13]=2)[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12171alpha,alpha'-Dichloro-p-xyleneHCID 31268PyrrolidineHCID 25020457N-Cyclopropyl-4-methyl-3-(1-oxo-1,2-dihydro-isoquinolin-6-yl)-benzamide

Product 1

HCID 25020779N-Cyclopropyl-4-methyl-3-(1-oxo-2-(4-(pyrrolidin-1-ylmethyl)benzyl)-1,2-dihydroisoquinolin-6-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of potassium carbonate (0.34 g), the product of Example 11 (0.1 g) and 1,4-bis(chloromethyl)benzene (0.220 g) in DMF (2 mL) was stirred at room temperature for 2.5 hours. To the reaction mixture was added pyrrolidine (0.3 mL) and stirring continued for a further 64 hours. The reaction mixture was filtered and the filtrate washed with methanol. The liquors were purified by HPLC to give the title compound as a solid (0.095 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate washed with methanol
  3. customThe liquors were purified by HPLC

Sources & evidence

ORD record
ord-9410d773de394076bab54f6a22b4f281
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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