Diisopropylethylamine → 2-(Azetidin-1-yl)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17405

Reaction equation

Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[F:11])[N:6]=1.C([N:24]([CH:27]([CH3:29])C)[CH2:25]C)(C)C.Cl.N1CCC1>ClCCl.C(O)C>[N:24]1([C:2]2[O:3][C:4]3[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:10]=3[F:11])[N:6]=2)[CH2:25][CH2:29][CH2:27]1

Participants

Conditions

Temperature: 60 °C

Procedure

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-130) (0.11 g, 0.38 mmol) was dissolved in a mixed solvent of dichloromethane (10 ml) and ethanol (7 ml), then diisopropylethylamine (0.21 ml, 1.23 mol) and azetidine hydrochloride (71.5 mg, 0.76 mmol) were added. After stirring at an external temperature of about 60° C. for 3 hours, the reaction liquid was concentrated under reduced pressure and diluted with dichloromethane. After washing with water and drying over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure and the resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=100:1) to obtain a colorless solid (85 mg, 74%).

Workup

customthe reaction liquid
concentrationwas concentrated under reduced pressure
additiondiluted with dichloromethane
washAfter washing with water
dry with materialdrying over anhydrous sodium sulfate
customthe solvent was evaporated away under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=100:1)

Sources & evidence

ORD record: ord-82c3a8fc81a14a919363875a9edbf55d
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Linked notes

Loading…