Trifluoroacetic acid → HCID 68830743, compound

Participants

Reaction Steps

Deprotection of N1-BOC-(1S,3R)-3-(2H-indazol-2-ylmethyl)cyclopentan-1-amine (400 mg, 1.27 mmol), the more polar isomer from Step 1, Example 67, using TFA (3 ml) in dry dichloromethane (3 ml) as described in Example 1, Step 2 gave 273 mg of the amine as its TFA salt, which was used as such for the coupling reaction. Step 2: Coupling reaction of Step 1 intermediate (273 mg, 1.27 mmol) with Intermediate 17 (109 mg, 0.63 mmol) in the presence of potassium carbonate (175 mg, 1.27 mmol) and NaI (95 mg, 0.63 mmol) in THF (30 ml) as described in Example 1, Step 3 gave 90 mg of the product as a yellow semisolid; IR (neat) 3317, 3117, 3058, 2943, 2872, 2239, 1660, 1514, 1412, 1306, 1262, 1191, 1157, 1139, 1042, 1009 cm−1; 1H NMR (CDCl3, 300 MHz) δ 1.14–1.29 (m, 2H), 1.53–1.62 (m, 2H), 1.74–1.90 (m, 3H), 1.95–2.32 (m, 5H), 2.67–2.73 (m, 1H), 3.12–3.17 (m, 1H), 3.35 (s, 2H), 3.37–3.59 (m, 2H), 4.38–4.41 (m, 2H), 4.74 (m, 1H), 7.04–7.09 (m, 1H), 7.26–7.30 (m, 1H), 7.64–7.71 (m, 2H), 7.92 (s, 1H).

Provenance & Evidence