Trifluoroacetic acid → HCID 10510985, compound

Participants

Reaction Steps

To a solution of 49 (43 mg, 0.17 mmol) in CH2Cl2 (0.8 mL) at 0° C. was added TFA (1.5 mL, excess), the ice bath was removed and the resultant solution was stirred at ambient temperature for 1 h. The solvent and excess TFA were removed under a stream of argon and the residue was dissolved in HCl(aq) (1.0 M, 1 mL) and washed with CH2Cl2 (3×10 mL). To the aqueous fraction was added CH2Cl2 (8 mL) and water (8 mL) and the pH was adjusted to 10 with NaOH(aq) (10 N) while stirring. The organic fraction was collected and the aqueous layer was extracted with CH2Cl2 (2×10 mL). The combined organic fractions were dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (CH3OH/CHCl3, 10/90, Rf=0.16) to afford the title compound 50 (13 mg, 53% yield) as an orange oil: 1H NMR (CDCl3) δ 8.65 (m, 1H), 8.51 (m, 1H), 7.07 (m, 1H), 7.23 (m, 1H), 3.64 (br s, 2H), 2.50 (br s, 3H); LRMS (ESI) m/z calcd for C9H11N2 [M+H]+ 147. found 147; LRMS (ESI) m/z calcd for C8H6N [M−NH(CH3)]+ 116. found 116; HRMS (ESI) m/z calcd for C9H11N2 [M+H]+ 147.0922. found 147.0921; HPLC>98% (tR=7.25 min, 60 (A):40 (B): 0.02 (C); tR=2.91 min, 60 (A):40 (B): 0.07 (C)).

Provenance & Evidence