Dimethylformamide → 1-[4-[(3-Chloro-4-methoxybenzyl)amino]-6-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)-1-phthalazinyl]-4-piperidinol

HRID 2300181Notes

Reaction equation

HRID 2300181 reaction equation
CI.[Cl:3][C:4]1[CH:5]=[C:6]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[NH:23][N:22]=[N:21][N:20]=3)[CH:17]=2)[C:12]([N:24]2[CH2:29][CH2:28][CH:27]([OH:30])[CH2:26][CH2:25]2)=[N:11][N:10]=1.[C:36](=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[N:23]([CH3:36])[N:22]=[N:21][N:20]=3)[CH:17]=2)[C:12]([N:24]2[CH2:25][CH2:26][CH:27]([OH:30])[CH2:28][CH2:29]2)=[N:11][N:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178491038HCID 178491038, compound

Product 1

HCID 227444841-[4-[(3-Chloro-4-methoxybenzyl)amino]-6-(1-methyl-1H-1,2,3,4-tetrazol-5-yl)-1-phthalazinyl]-4-piperidinolYield 19.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.037 ml methyl iodide was added to a mixture of 0.25 g 1-[4-[(3-chloro-4-methoxybenzyl)amino]-6-(1H-1,2,3,4-tetrazole-5-yl)-1-phthalazinyl]-4-piperidinol, 1.2 g potassium carbonate and 5 ml dimethylformamide, and stirred at room temperature for 3 hr. Water was added to the reaction solution, and the precipitated insoluble matters were collected by filtration. Then, purified by silica gel column chromatography to give 50 mg of the title compound.

Workup

  1. filtrationthe precipitated insoluble matters were collected by filtration
  2. customThen, purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e0e20527de9a42239062486372472d71
Source dataset
uspto-grants-2002_12
Patent number
US06498159B1

Reaction notes

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