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

HRID 1917116Notes

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.Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[C:33]([F:36])([F:35])[F:34].O>C1(C)C=CC=CC=1>[F:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:14]2[CH2:13][CH2:12][N:11]([C:4]3[C:5](=[O:10])[N:6]([CH3:9])[C:7](=[O:8])[N:2]([CH3:1])[N:3]=3)[CH2:16][CH2:15]2)=[C:27]([C:33]([F:34])([F:35])[F:36])[CH:28]=1

Participants

Conditions

Temperature: 110 °C

Procedure

The compound 54 is prepared according to the synthesis method 2: 0.26 g (1.17 mmol) of derivative 12a is placed in 3 mL of toluene in the presence of 0.24 mL (1.75 mmol) of NEt3 and of 0.3 g (1.17 mmol) of 1-bromomethyl-4-fluoro-2-trifluoromethyl-benzene. This mixture is stirred 2 h at 110° C. The medium is taken up with water and extracted with AcOEt. After drying on MgSO4, the organic phase is dry concentrated. The obtained residue is purified by flash chromatography on silica (CH2Cl2-AcOEt: 95-5). 0.37 g of a yellow oil are isolated (yield: 79%).

Workup

customaccording to the synthesis method 2
extractionextracted with AcOEt
customAfter drying on MgSO4
customthe organic phase is dry
concentrationconcentrated
customThe obtained residue is purified by flash chromatography on silica (CH2Cl2-AcOEt: 95-5)

Sources & evidence

ORD record: ord-951704f6ac7d4b60a0e5a81e155aecf0
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618287B2

Reaction notes

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