Triethylamine → 2-Cyclopent-1-enyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17508Notes

Reaction equation

[C:1]1([C:6]2[O:7][C:8]3[C:9](=[C:11]([C:23]#[N:24])[C:12]([CH3:22])=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:14]=3F)[N:10]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1.C(N(CC)CC)C.[CH3:32][N:33]([CH3:39])[C@H:34]1[CH2:38][CH2:37][NH:36][CH2:35]1>CS(C)=O>[C:1]1([C:6]2[O:7][C:8]3[C:9](=[C:11]([C:23]#[N:24])[C:12]([CH3:22])=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:14]=3[N:36]3[CH2:37][CH2:38][C@H:34]([N:33]([CH3:39])[CH3:32])[CH2:35]3)[N:10]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

Conditions

Temperature: 95 °C

Procedure

2-(Cyclopent-1-en-1-yl)-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-214) (145 mg, 0.46 mmol) was dissolved in dimethyl sulfoxide (5 ml), then triethylamine (130 μl, 0.91 mmol) and (3S)-3-(dimethylamino)pyrrolidine (121 μl, 0.96 mmol) were added, followed by stirring at 95° 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 subjected to preparative silica gel column chromatography. The eluate with chloroform/methanol (5:1, y/v) gave the entitled compound (34 mg, 18%) as a pale yellow amorphous substance.

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

Sources & evidence

ORD record: ord-1d8b10cebba949ba8ee2379a2765ebcd
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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