Triethylamine → HCID 136395114, compound

HRID 641220Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][C:5]=1[C:14]1[NH:19][C:18](=[O:20])[C:17]2=[C:21]([CH3:27])[N:22]=[C:23]([CH2:24][CH2:25][CH3:26])[N:16]2[N:15]=1)[CH3:2].FC(F)(F)C(O)=O.[CH3:35][N:36]1[O:40][NH+:39]([O-:41])[CH:38]=[C:37]1[C:42]([N:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1)=[O:43].C(N(CC)CC)C>ClCCl>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:47]2[CH2:46][CH2:45][N:44]([C:42]([C:37]3[N:36]([CH3:35])[O:40][NH+:39]([O-:41])[CH:38]=3)=[O:43])[CH2:49][CH2:48]2)(=[O:12])=[O:11])=[CH:6][C:5]=1[C:14]1[NH:19][C:18](=[O:20])[C:17]2=[C:21]([CH3:27])[N:22]=[C:23]([CH2:24][CH2:25][CH3:26])[N:16]2[N:15]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

410 mg (1.0 mmol) of 4-ethoxy-3-(5-methyl-4-oxo-7-propyl-3,4-dihydro-imidazo[5,1-f][1,2,4]triazin-2-yl)-benzenesulphonyl chloride are dissolved in 10 ml of dichloromethane and cooled to 0° C. 590 mg (2.00 mmol) of 1-(5-methyl-4-furoxanecarbonyl)-piperazine trifluoroacetate and 400 mg of triethylamine are added, and the reaction mixture is stirred at room temperature overnight. The mixture is diluted with dichloromethane, the organic phase is washed with ammonium chloride solution, 1M hydrochloric acid and water and dried over sodium sulphate and the solvent is removed under reduced pressure. Crystallization from ether gives 448 mg (74%) of a colourless solid.

Workup

washthe organic phase is washed with ammonium chloride solution, 1M hydrochloric acid and water
dry with materialdried over sodium sulphate
customthe solvent is removed under reduced pressure
customCrystallization from ether

Sources & evidence

ORD record: ord-19081f48f46047ba940447f5ef02310a
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696206B2

Reaction notes

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