Triethylamine → HCID 68584851, compound

HRID 17419Notes

Reaction equation

F[C:2]1[C:3]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([CH3:18])[C:5]([C:16]#[N:17])=[C:6]2[C:10]=1[O:9][C:8]([N:11]1[CH2:14][CH:13]([OH:15])[CH2:12]1)=[N:7]2.[CH3:25][N:26]([CH3:32])[C@H:27]1[CH2:31][CH2:30][NH:29][CH2:28]1.C(N(CC)CC)C>CS(C)=O>[CH3:25][N:26]([CH3:32])[C@H:27]1[CH2:31][CH2:30][N:29]([C:2]2[C:3]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:4]([CH3:18])[C:5]([C:16]#[N:17])=[C:6]3[C:10]=2[O:9][C:8]([N:11]2[CH2:14][CH:13]([OH:15])[CH2:12]2)=[N:7]3)[CH2:28]1

Participants

Conditions

Temperature: 150 °C

Procedure

7-Fluoro-2-(3-hydroxyazetidin-1-yl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-143) (120 mg, 0.37 mmol) was dissolved in dimethyl sulfoxide (6 ml), then (3S)-3-(dimethylamino)pyrrolidine (71 μl, 0.56 mmol) and triethylamine (189 μl, 1.11 mmol) were added, followed by stirring at 150° C. under nitrogen atmosphere for 5 hours. After cooling and fractionation with water and ethyl acetate, the organic layer was washed with saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative silica gel column chromatography. Elution with a mixed solvent of chloroform/methanol (9:1, v/v/) gave the entitled compound (36.4 mg, 23%) as a white solid.

Workup

temperatureAfter cooling
washfractionation with water and ethyl acetate, the organic layer was washed with saturated brine
dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
customthe solvent was evaporated away under reduced pressure
washElution with a mixed solvent of chloroform/methanol (9:1, v/v/)

Sources & evidence

ORD record: ord-8c66538e6d7b4a858829710582fb2f52
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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