Triethylamine → HCID 68587044, compound

HRID 17609Notes

Reaction equation

[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:18]#[N:19])[C:10]([CH3:17])=[C:11]([C:14]([CH3:16])=[CH2:15])[C:12]=3F)[N:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:27][N:28]([CH3:34])[C@H:29]1[CH2:33][CH2:32][NH:31][CH2:30]1>CSC>[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:18]#[N:19])[C:10]([CH3:17])=[C:11]([C:14]([CH3:16])=[CH2:15])[C:12]=3[N:31]3[CH2:32][CH2:33][C@H:29]([N:28]([CH3:34])[CH3:27])[CH2:30]3)[N:8]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

2-Cyclopropyl-7-fluoro-6-isopropenyl-5-methyl-1,3-benzoxazole-4-carbonitrile (I-315) (34 mg, 0.13 mmol) was dissolved in dimethyl sulfide (2 ml), then triethylamine (38 μl, 0.27 mmol) and (3S)-3-(dimethylamino)pyrrolidine (36 μl, 0.28 mmol) were added, followed by stirring under nitrogen atmosphere at 90° C. for 4 hours. After cooled, this was concentrated under reduced pressure, diluted with chloroform and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (21 mg, 25%) as a brown crystal.

Workup

temperatureAfter cooled
concentrationthis was concentrated under reduced pressure
additiondiluted with chloroform
washwashed with saturated brine
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated away under reduced pressure
customThe resulting residue was purified by preparative TLC (eluent, chloroform

Sources & evidence

ORD record: ord-81fd409dc70646578783faff6114b640
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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