Structure–Activity Relationships for Development of Neurokinin-3 Receptor Antagonists by Koki Yamamoto
Author:Koki Yamamoto
Language: eng
Format: epub
ISBN: 9789811529658
Publisher: Springer Singapore
2-Methoxy-N-[2-(N-propargyl-N-tosylamino)ethyl]-N′-tosylbenzohydrazonamide (1c). By use of a procedure similar to that described for the preparation of the compound 1a from 8a, the compound 8c (57.9 mg, 0.150 mmol) was converted to the title compounds 1Xc and 1Yc (63.8 mg, 77%; 70:30 mixture): colorless amorphous solid; IR (neat) 1599 (C=N), 1331 (NSO2), 1160 (NSO2) cm−1; 1H NMR (1Xc, 500 MHz, CDCl3) δ 2.04–2.06 (m, 1H), 2.42 (s, 3H), 2.43 (s, 3H), 3.36 (t, J = 5.4 Hz, 2H), 3.45–3.48 (m, 2H), 3.75 (s, 3H), 4.07 (d, J = 2.3 Hz, 2H), 4.41 (br s, 1H), 6.91–6.94 (m, 1H), 6.98–7.02 (m, 1H), 7.13–7.15 (m, 1H), 7.28–7.31 (m, 4H), 7.39–7.43 (m, 1H), 7.70 (d, J = 8.6 Hz, 2H), 7.80–7.81 (m, 2H); 13C NMR (1Xc, 125 MHz, CDCl3) δ 21.6 (2C), 37.0, 39.6, 45.3, 55.7, 74.0, 76.6, 111.0, 120.9, 121.6, 127.7 (2C), 128.2 (3C), 129.2 (3C), 129.6 (2C), 130.6, 131.9, 135.4, 143.8, 154.7, 155.4; 1H NMR (1Yc, 500 MHz, CDCl3) δ 2.04–2.06 (m, 1H), 2.38 (s, 3H), 2.42 (s, 3H), 3.16–3.24 (m, 4H), 3.84 (s, 3H), 3.99 (d, J = 2.3 Hz, 2H), 6.66 (br s, 1H), 6.91–6.94 (m, 1H), 6.98–7.02 (m, 1H), 7.22–7.24 (m, 1H), 7.28–7.31 (m, 4H), 7.39–7.43 (m, 1H), 7.66 (d, J = 8.0 Hz, 2H), 7.82 (d, J = 8.0 Hz, 2H); 13C NMR (1Yc, 125 MHz, CDCl3) δ 21.6 (2C), 37.9, 42.3, 47.2, 55.6, 74.1, 76.9, 111.4, 120.5, 121.6, 127.7 (3C), 128.2 (3C), 129.4 (4C), 130.6, 131.6, 135.6, 143.2, 155.4, 156.7; HRMS (ESI) calcd for C27H31N4O5S2 [M + H]+: 555.1730, found: 555.1738.
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