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

HRID 17450Notes

Reaction equation

[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:22]#[N:23])[C:10]([CH3:21])=[C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[F:20])[C:12]=3F)[N:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:31][N:32]([CH3:38])[C@H:33]1[CH2:37][CH2:36][NH:35][CH2:34]1.C(=O)([O-])O.[Na+]>CS(C)=O.C(OCC)(=O)C>[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:22]#[N:23])[C:10]([CH3:21])=[C:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[F:20])[C:12]=3[N:35]3[CH2:36][CH2:37][C@H:33]([N:32]([CH3:38])[CH3:31])[CH2:34]3)[N:8]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

2-Cyclopropyl-7-fluoro-6-(2-fluorophenyl)-5-methyl-1,3-benzoxazole-4-carbonitrile (I-175) (147 mg, 0.47 mmol) was dissolved in dimethyl sulfoxide (3 ml), then at room temperature, triethylamine (99 μl, 0.71 mmol) and (3S)-3-(dimethylamino)pyrrolidine (78 μl, 0.62 mmol) were added. The solution was stirred under nitrogen atmosphere at 90° C. for 10 hours. After cooling to room temperature, the reaction liquid was fractionated with ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution.

Workup

temperatureAfter cooling to room temperature
customthe reaction liquid

Sources & evidence

ORD record: ord-48b8a2f3441d4317bc68e5754a998633
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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