Triethylamine → HCID 68587517, compound

HRID 17615Notes

Reaction equation

[CH3:1][N:2]([CH3:19])[C:3]1[C:4](F)=[C:5]2[O:9][C:8]([CH:10]3[CH2:12][CH2:11]3)=[N:7][C:6]2=[C:13]([C:16]#[N:17])[C:14]=1[CH3:15].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:10]1([C:8]2[O:9][C:5]3[C:6](=[C:13]([C:16]#[N:17])[C:14]([CH3:15])=[C:3]([N:2]([CH3:19])[CH3:1])[C:4]=3[N:31]3[CH2:32][CH2:33][C@H:29]([N:28]([CH3:34])[CH3:27])[CH2:30]3)[N:7]=2)[CH2:12][CH2:11]1

Participants

Conditions

Temperature: 100 °C

Procedure

6-Dimethylamino-2-Cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-321) (34 mg, 0.10 mmol) was dissolved in dimethyl sulfide (4 ml), then triethylamine (29 μl, 0.20 mmol) and (3S)-3-(dimethylamino)pyrrolidine (27 μl, 0.21 mmol) were added, followed by stirring under nitrogen atmosphere at 100° C. for 24 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 (20 mg, 64%) as a white 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-35ec36a70f0a4dd59673a3969f3763e7
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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