Hydrochloric Acid → (S)-(3-Fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methanamine Hydrochloride

HRID 2370751

Reaction equation

[F:1][C:2]1[C:3]([C@H:8]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[NH:9][S@](C(C)(C)C)=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[ClH:26].CCOC(C)=O>C(Cl)Cl.CCO.O1CCOCC1>[ClH:26].[F:1][C:2]1[C:3]([C@H:8]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][CH:17]=2)[NH2:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) stirring solution of (S)—N—((S)-(3-fluoropyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)-2-methylpropane-2-sulfinamide (108 g, 288.8 mmol) in DCM:EtOH (1:1, 1080 mL), was added saturated HCl in 1,4-dioxane (216 mL). Stirring was continued for 2 h at 0° C. The progress of the reaction was monitored by TLC (100% EtOAc). After completion of the reaction, the reaction mixture was concentrated and triturated with Et2O to give a white solid which was filtered and dried to give the title compound as a white solid. 1H-NMR (400 MHz, CDCl3) δ ppm 9.23 (s, 3H), 8.60 (d, J=4.8 Hz, 1H), 7.87 (d, J=1.2 Hz, 1H), 7.84 (d, J=8.4 Hz, 2H), 7.72 (d, J=8.4 Hz, 2H), 7.59-7.63 (m, 1H), 6.09 (s, 1H). MS (ESI pos. ion) m/z: 270.1 (M+H).

Workup

customAfter completion of the reaction
concentrationthe reaction mixture was concentrated
customtriturated with Et2O
customto give a white solid which
filtrationwas filtered
customdried

Sources & evidence

ORD record: ord-8daa5422afae40428c50fb011677b76c
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710043B2

Linked notes

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