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

HRID 47345Notes

Reaction equation

HRID 47345 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-8e3a1e0fe7a84672a8776f5b683b0849
Source dataset
uspto-grants-2004_03
Patent number
US06699870B2

Reaction notes

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