Ethyl Acetate → [4-(4-[1,2,3]Triazol-1-yl-butyl)-phenyl]-{2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethyl}-amine

HRID 1271435Notes

Reaction equation

[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].Cl[CH2:20][C:21]1[N:22]=[C:23]([CH:26]=[CH:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=2)[O:24][CH:25]=1.C(OCC)(=O)C>CN(C)C=O>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][CH2:20][C:21]3[N:22]=[C:23]([CH:26]=[CH:27][C:28]4[CH:29]=[CH:30][C:31]([O:34][C:35]([F:38])([F:36])[F:37])=[CH:32][CH:33]=4)[O:24][CH:25]=3)=[CH:14][CH:15]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

4-(4-[1,2,3]Triazol-1-yl-butyl)-phenylamine (0.304 g, 1 mmol) is dissolved in anhydrous N,N-dimethylformamide (5 ml) followed by the addition of sodium hydride (0.024 g, 1 mmol). After stirring for 15 min at room temperature 4-chloromethyl-2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazole (0.324 g, 1.5 mmol) is added and the mixture stirred for 16 h at 80° C. Ethyl acetate (25 ml) is added, the mixture is washed with brine, dried over sodium sulfate and concentrated in vacuo. After flash column chromatography (ethyl acetate/hexanes 1:1->2:1) [4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-{2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethyl}-amine 1 can be isolated as a yellow solid. Yield 0.14 g (29%); m.p. 103–105° C.

Workup

additionis added
washthe mixture is washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-10ee6d7697a940929d5c14dcf4cf790d
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07205326B2

Reaction notes

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