2-Dimethylaminopyridine → HCID 135856769, compound

HRID 641223Notes

Reaction equation

HRID 641223 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]2[NH:15][C:14](=[O:16])[C:13]3=[C:17]([CH3:23])[N:18]=[C:19]([CH2:20][CH2:21][CH3:22])[N:12]3[N:11]=2)=[CH:8][C:7]([S:24](Cl)(=[O:26])=[O:25])=[C:6]([O:28][CH3:29])[CH:5]=1)[CH3:2].CN(C1C=CC=CN=1)C.[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>ClCCl>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:28][CH3:29])[C:7]([S:24]([N:43]2[CH2:44][CH2:45][N:40]([CH3:39])[CH2:41][CH2:42]2)(=[O:26])=[O:25])=[CH:8][C:9]=1[C:10]1[NH:15][C:14](=[O:16])[C:13]2=[C:17]([CH3:23])[N:18]=[C:19]([CH2:20][CH2:21][CH3:22])[N:12]2[N:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 531671-MethylpiperazineHCID 135856755HCID 135856755, compound

Product 1

HCID 135856769HCID 135856769, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

20 mg (0.045 mmol) of 4-ethoxy-2-methoxy-5-(5-methyl-4-oxo-7-propyl-3,4-dihydroimidazo-[5,1-f][1,2,4]triazin-2-yl)-benzenesulphonyl chloride are dissolved in 0.5 ml of dichloromethane and admixed with a spatula tip of dimethylaminopyridine and 14 mg (0.136 mmol) of N-methylpiperazine, and the reaction mixture is stirred at room temperature overnight. Purification over silica gel gives 12.8 mg (55%) of 2-[2-ethoxy-4-methoxy-5-(4-methylpiperazine-1-sulphonyl)phenyl]-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one.

Workup

  1. customPurification over silica gel

Sources & evidence

ORD record
ord-453429533adb4d3b8d41dac8d4b67d23
Source dataset
uspto-grants-2010_04
Patent number
US07696206B2

Reaction notes

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