Trifluoroacetic acid → (S)-(4-(Trifluoromethyl)phenyl)(3-vinylpyridin-2-yl)methanamine 2,2,2-trifluoroacetate

HRID 509375Notes

Reaction equation

[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([NH:18]C(=O)OC(C)(C)C)[C:10]2[C:15]([CH:16]=[CH2:17])=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1.[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29]>C(Cl)Cl>[F:31][C:30]([F:33])([F:32])[C:28]([OH:34])=[O:29].[F:27][C:2]([F:1])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([C:10]2[C:15]([CH:16]=[CH2:17])=[CH:14][CH:13]=[CH:12][N:11]=2)[NH2:18])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a 50 mL round bottom flask containing (S)-tert-butyl ((4-(trifluoromethyl)phenyl)(3-vinylpyridin-2-yl)methyl)carbamate (97 mg, 0.256 mmol) was added DCM (3 mL). The resulting mixture was then stirred at 23° C. for 2 min. At this time, TFA was added (3 mL) and the reaction was stirred for 3 h. The solvent was removed, and the material was immediately used with no further purification. MS (ESI pos. ion) m/z: 279.1 (M+1).

Workup

stirringthe reaction was stirred for 3 h
customThe solvent was removed
customthe material was immediately used with no further purification

Sources & evidence

ORD record: ord-8518d249bde84fc290fa8bc562bd8ff0
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096527B2

Reaction notes

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