Dimethylamine → 7-Fluoro-2-(dimethylamino)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17401Notes

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.[CH:21]([N:24](C(C)C)[CH2:25]C)(C)C.CNC>ClCCl>[F:11][C:10]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([CH3:18])[C:7]([C:19]#[N:20])=[C:5]2[C:4]=1[O:3][C:2]([N:24]([CH3:25])[CH3:21])=[N:6]2

Participants

Conditions

Temperature: 60 °C

Procedure

2-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (0.20 g, 0.70 mmol) was dissolved in dichloromethane (7 ml), then diisopropylethylamine (0.15 ml, 0.88 mmol), dimethylamine (2.0 M tetrahydrofuran solution, 0.50 ml, 1.00 mmol) were added. After stirring in a sealed tube at an external temperature of about 60° C. for 3 hours, this was 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) to obtain a colorless solid (0.18 g, 87%).

Workup

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)

Sources & evidence

ORD record: ord-82d35c9b1e364f908b3a284a20e81a39
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

Loading…