Triethylamine → HCID 136395114, compound

HRID 2249455Notes

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-a812e1e01c0844f4a891317992f9ab5b
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314871B2

Reaction notes

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