Allylamine → HCID 68460320, compound

Participants

Reaction Steps

The product from Example 208d (60 mg, 0.147 mmol) was dissolved in THF to which was added N-methyl morpholine (49 mg, 0.162 mmol), and isopropenyl chloroformate (36 mg, 0.295 mmol). This was stirred at room temperature for 1 hr at which time the allylamine (42 mg, 0.739 mmol) was added and the reaction mixture stirred at room temperature for another 1 hr. THF was then removed under a stream of N2 and then crude oil was purified by HPLC with TFA providing the product as a trifluoroacetic acid. (8.0 mg, 9.5%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.92 (s, 3H), 2.74 (s, 2 H), 3.86 (d, J=5.15 Hz, 2 H), 5.04-5.16 (m, 2 H), 5.73-5.98 (m, 1 H), 6.73 (d, J=6.99 Hz, 1 H), 7.10 (dd, J=7.72, 2.21 Hz, 1 H), 7.27-7.43 (m, 3 H), 7.51-7.65 (m, 2 H), 7.69-7.82 (m, 2H), 8.54 (d, J=7.35 Hz, 1 H), 8.82 (d, J=8.46 Hz, 1 H); MS (ESI+) m/z 445 (M+TFA+H)+; (ESI−) m/z 443 (M+TFA−H)−.

Provenance & Evidence