Trifluoroacetic acid → HCID 10006445, compound

Participants

Reaction Steps

Using the same method as for COMPOUND 17 and using INTERMEDIATE 5a (209 mg, 0.45 mmol), 2-quinolinecarboxaldehyde (77.6 mg, 0.49 mmol), and decaborane (16.4 mg, 0.13 mmol) afforded COMPOUND 54 (162 mg, 38% yield) as its TFA salt. This material was lyophilized from CH3CN/H2O to produce a yellow solid. Purity (HPLC): >98%; Optical purity (Chiral HPLC): >99%; 1H NMR (400 MHz, CD3OD) δ 1.07 (br t, J=6.7 Hz, 3H), 1.23 (br t, J=6.6 Hz, 3H), 2.59 (br s, 4H), 3.18 (br t, J=4.4 Hz, 6H), 3.52 (br q, J=7.2 Hz, 2H), 4.30 (s, 1H), 4.89 (s, 2H), 6.58 (dd, J=7.9, 2.1 Hz, 1H), 6.72 (s, 1H), 6.82 (d, J=7.4 Hz, 1H), 7.04-7.12 (m, 3H), 7.36 (d, J=8.2 Hz, 2H), 7.85-7.93 (m, 2H), 8.09 (td, J=7.8, 1.2 Hz, 1H), 8.22 (d, J=8.2 Hz, 1H), 8.27 (d, J=8.4 Hz, 1H), 8.87 (d, J=8.6 Hz, 1H). Found: C, 50.15; H, 4.57; N, 7.46. C32H37N5O×1.1 H2O×3.6 CF3COOH has C, 50.20; H, 4.60; N, 7.47%. [α]D17=+20.8 deg [c 0.726, MeOH].

Provenance & Evidence