Water → 6-[4-(2,5-Bis-trifluoromethyl-benzoyl)-piperazin-1-yl]-2,4-dimethyl-2H-[1,2,4]triazine-3,5-dione

HRID 1917111Notes

Reaction equation

[CH3:1][N:2]1[C:7](=[O:8])[N:6]([CH3:9])[C:5](=[O:10])[C:4]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[N:3]1.CCN(CC)CC.[F:24][C:25]([F:40])([F:39])[C:26]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][C:27]=1[C:28](Cl)=[O:29].O>ClCCl>[F:24][C:25]([F:39])([F:40])[C:26]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:31][C:27]=1[C:28]([N:14]1[CH2:13][CH2:12][N:11]([C:4]2[C:5](=[O:10])[N:6]([CH3:9])[C:7](=[O:8])[N:2]([CH3:1])[N:3]=2)[CH2:16][CH2:15]1)=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

The compound 40 is prepared according to the synthesis method 2: 0.16 g (0.72 mmol) of derivative 12a is placed in 1 mL of dichloromethane in the presence of 0.15 mL (1.08 mmol) of NEt3 at 0° C. 0.2 g (0.72 mmol) of 2,5-bis-trifluoromethyl-benzoyl chloride is added. This mixture is stirred for 15 min at 0° C., and then for 1 h at room temperature. The medium is taken up with water and extracted with CH2Cl2. After drying on MgSO4, the organic phase is concentrated. The obtained residue is purified by flash chromatography on silica (CH2Cl2-AcOEt: 90-10). 0.24 g of white crystals are isolated (yield: 71%).

Workup

customaccording to the synthesis method 2
waitfor 1 h at room temperature
extractionextracted with CH2Cl2
customAfter drying on MgSO4
concentrationthe organic phase is concentrated
customThe obtained residue is purified by flash chromatography on silica (CH2Cl2-AcOEt: 90-10)

Sources & evidence

ORD record: ord-e5ff31a155654090a5aeca0ed8a9a43d
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618287B2

Reaction notes

Loading…