Triethylamine → HCID 68584644, compound

HRID 17406Notes

Reaction equation

[N:1]1([C:5]2[O:6][C:7]3[C:8](=[C:10]([C:22]#[N:23])[C:11]([CH3:21])=[C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:13]=3F)[N:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:24]([N:26]([CH2:29]C)[CH2:27][CH3:28])C.[NH:31]1CC[CH2:33][CH2:32]1>CS(C)=O.ClCCl>[N:1]1([C:5]2[O:6][C:7]3[C:8](=[C:10]([C:22]#[N:23])[C:11]([CH3:21])=[C:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:13]=3[N:31]3[CH2:32][CH2:33][C@H:27]([N:26]([CH3:24])[CH3:29])[CH2:28]3)[N:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 150 °C

Procedure

2-(Azetidin-1-yl)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-134) (0.11 g, 0.36 mmol) was dissolved in dimethyl sulfoxide (3.5 ml), then triethylamine (0.10 ml, 0.72 mmol) and (3S)-3-dimethylamino)pyrrolidine (92.0 μl, 0.73 mmol) were added, followed by stirring in a sealed tube at an external temperature of about 150° C. for 4 hours. This was diluted with dichloromethane, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=20:1), then diisopropyl ether was added, and the insoluble matter was collected by filtration to obtain a pale beige solid (23 mg, 17%).

Workup

washwashed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated away under reduced pressure
customthe resulting residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=20:1)
additiondiisopropyl ether was added
filtrationthe insoluble matter was collected by filtration

Sources & evidence

ORD record: ord-dd66c21ae78448029bbd4b0f2bc20496
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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