Compound 103
(S)-4-(3-(azetidin-1-yl)benzyl)-2-(6-((S)-4-(4-(azetidin-1-yl)benzyl)-4,5-dihydrooxazol-2-yl)pyridin-2-yl)-4,5-dihydrooxazole
From: Practical and regioselective amination of arenes using alkyl amines
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Compound data: NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Following GP2 outlined for compound 45, in 1,1,1,3,3,3-hexafluoro-i-propanol (HFIP) at 0 °C but using 1.0 equiv. of 2,6-bis((S)-4-benzyl-4,5-dihydrooxazol-2-yl)pyridine, 2.8 equiv. of azetidine hydrochloride, 2.8 equiv.of NCS, 2.6 of equiv. of N,N-diisopropylehtylamine and 8.0 equiv. of HClO4, 2,6-bis((S)-4-benzyl-4,5-dihydrooxazol-2-yl)pyridine (49 mg, 0.1 mmol) gave 103 and 103* (48 mg, 90%) as a inseparable wax. 103:103* = 4:1. Rf 0.15 [CH2Cl2–Et2O–acetone (8:1.5:0.5)]; FT-IR νmax (film)/cm–1 3056, 2905, 1734, 1772, 1537, 1229, 1011; 1H NMR (CDCl3, 400 MHz) δ 8.21 (2H, dt, J = 7.8, 1.5 Hz), 7.88 (1H, tt, J = 7.9, 1.8 Hz), 7.14 (1H, t, J = 7.7 Hz), 7.07 (2H, d, J = 8.4 Hz), 6.59 (1H, d, J = 7.5 Hz), 6.40 (2H, d, J = 8.4 Hz), 6.32 (1H, d, J = 8.0 Hz), 6.29 (1H, s), 4.67 – 4.54 (2H, m,), 4.43 (2H, t, J =9 .0 Hz), 4.26 (1H, t, J = 8.1 Hz), 4.25 (1H, t, J = 8.2 Hz), 3.88 – 3.80 (8H, m), 3.24 (1H, ABq, JAB = 13.6, 4.8 Hz), 3.18 (1H, ABq, JAB = 13.8, 4.9 Hz), 2.67 – 2.57 (2H, m), 2.34 (4H, p, J=7.2 Hz); 13C NMR (CDCl3, 101 MHz) δ 162.8, 162.8, 152.6, 151.2, 147.0, 147.0, 138.6, 137.5, 129.8, 129.3, 126.3, 125.8, 118.2, 112.2, 111.8, 109.8, 72.8, 68.6, 68.2, 52.7, 52.5, 42.0, 41.0, 17.2, 17.1. HRMS (ASAP POS): Found MH+ 508.2710., C30H45N8O6 requires 508.2707.
