Trifluoroacetic acid → HCID 18453453, compound

Participants

Reaction Steps

Deprotection of N1-BOC-[(3S,1R)-3-(2H-benzo[d][1,2,3]triazol-1-ylmethyl)cyclopentylamine (420 mg, 1.33 mmol), the less polar isomer from Step 1 using TFA (2 ml) in dry dichloromethane (2 ml) as described in Example 1, Step 2 gave 438 mg of the amine as its TFA salt, which was used as such for the next step. Step 3: Coupling reaction of Step 2 intermediate (438 mg, 1.33 mmol) with Intermediate 17 (160 mg, 0.93 mmol) in the presence of potassium carbonate (735 mg, 5.32 mmol) and NaI (140 mg, 0.93 mmol) in THF (30 ml) as described in Example 1, Step 3 gave 100 mg of the product as a white solid; IR (KBr) 3317, 2928, 2239, 1659, 1416, 1266 cm−1; 1H NMR (CDCl3, 300 MHz) δ 1.23–1.33 (m, 1H), 1.57–1.66 (m, 2H), 1.70–2.03 (m, 5H), 2.14–2.31 (m, 3H), 2.63–2.74 (m, 1H), 3.16–3.19 (m, 1H), 3.30–3.67 (m, 2H), 3.36 (d, J=6.6 Hz, 2H), 4.56–4.77 (m, 3H), 7.26–7.39 (m, 1H), 7.45–7.56 (m, 2H), 8.06 (d, J=8.1 Hz, 1H).

Provenance & Evidence