Triethylamine → N-(3-{5,7-Dimethyl-4-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-2-yl}phenyl)methanesulfonamide

HRID 1270320Notes

Reaction equation

HRID 1270320 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[C:11]3=[C:27]([CH3:31])[N:28]=[C:29]([CH3:30])[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34].C(N(CC)CC)C>ClCCl>[CH3:31][C:27]1[N:28]=[C:29]([CH3:30])[N:10]2[C:11]=1[C:12]([NH:14][C:15]1[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=1)=[N:13][C:8]([C:4]1[CH:3]=[C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])[CH:7]=[CH:6][CH:5]=1)=[N:9]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18449115N-[2-(3-Aminophenyl)-5,7-dimethylimidazo[5,1-f][1,2,4]triazin-4-yl]-N-(3,4,5-tri-methoxyphenyl)amine

Product 1

HCID 18449118N-(3-{5,7-Dimethyl-4-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-2-yl}phenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 80 mg (0.19 mmol) of 3-[5,7-dimethyl-4-(3,4,5-trimethoxyphenoxy)-imidazo[5,1-f][1,2,4]triazin-2-yl]aniline from example 7, 20 mg (0.19 mmol) of methanesulfonyl chloride and 40 mg (0.38 mmol) of triethylamine in dichloromethane is stirred overnight at 20° C. The mixture is washed with aqueous sodium hydrogencarbonate solution, and the organic phase is dried and purified by HPLC.

Workup

  1. washThe mixture is washed with aqueous sodium hydrogencarbonate solution
  2. customthe organic phase is dried
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-77a7138d7b7c4eafba845e4b2778a177
Source dataset
uspto-grants-2007_04
Patent number
US07202243B2

Reaction notes

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