1,3-Thiazole-2-carbaldehyde → (S)-3-[5-(1-Thiazol-2-ylmethyl-pyrrolidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile

Participants

Reaction Steps

3-[5-(1-Thiazol-2-ylmethyl-pyrrolidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile (63.5 mg, 91%) was obtained as described in Example 43 from (S)-3-(5-pyrrolidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile (49.8 mg, 0.18 mmol) reacted with thiazole-2-carbaldehyde (35.2 mg, 0.31 mmol) and sodium triacetoxyborohydride (72 mg, 0.34 mmol) is in dichloroethane (3 mL) at room temperature. 1H NMR (CDCl3), δ(ppm): 8.39 (s, 1H), 8.32 (d, 1H), 7.78 (d, 1H), 7.68 (d, 1H), 7.60 (t, 1H), 7.27 (d, 1H), 4.32 (dd, 1H), 4.27 (dab, 1H), 4.17 (dab, 1H), 3.31 (m, 1H), 2.81 (q, 1H), 2.39 (m, 1H), 2.25 (m, 1H), 2.14 (m, 1H), 2.04 (m, 1H).

Provenance & Evidence