Triethylamine → HCID 51042118, compound

HRID 17456Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](F)=[C:10]3[O:14][C:13]([CH:15]4[CH2:17][CH2:16]4)=[N:12][C:11]3=[C:18]([C:21]#[N:22])[C:19]=2[CH3:20])[CH:5]=[CH:6][CH:7]=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>[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([N:35]3[CH2:36][CH2:37][C@H:33]([N:32]([CH3:38])[CH3:31])[CH2:34]3)=[C:10]3[O:14][C:13]([CH:15]4[CH2:17][CH2:16]4)=[N:12][C:11]3=[C:18]([C:21]#[N:22])[C:19]=2[CH3:20])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

6-(3-Aminophenyl)-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-178) (200 mg, 0.65 mmol) was dissolved in dimethyl sulfoxide (4 ml), then at room temperature, triethylamine (136 μl, 0.98 mmol) and (3S)-3-(dimethylamino)pyrrolidine (124 μl, 0.98 mmol) were added. The solution was stirred under nitrogen atmosphere at 90° C. for 19 hours, then cooled to room temperature. This was fractionated with ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution.

Workup

temperaturecooled to room temperature

Sources & evidence

ORD record: ord-902a9ff84aca45ca9c38902439cd98a2
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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