6-Phenoxypyridine-3-sulphonyl chloride → Benzamide
반응식
NC[C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9]C2C=NC=CC=2)=[O:8])=[CH:5][CH:4]=1.O(C1N=CC(S(Cl)(=O)=O)=CC=1)C1C=CC=CC=1>N1C=CC=CC=1>[C:7]([NH2:9])(=[O:8])[C:6]1[CH:16]=[CH:17][CH:3]=[CH:4][CH:5]=1참가 물질
4
반응 조건
- 온도
- 20 °C
실험 절차
A mixture of 4-(aminomethyl)-N-(3-pyridinyl)benzamide (33) (464 mg, 2.0 mmol) and 6-phenoxy-3-pyridinesulfonyl chloride (606 mg, 2.2 mmol) in dry pyridine (10 mL) was stirred at 20° C. for 16 h. The solvent was evaporated and the residue stirred in ice/water (20 mL) for 1 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with a gradient (0-20%) of MeOH/EtOAc, to give benzamide I-3 (405 mg, 43%) as a white powder: mp (MeOH/EtOAc) 203-205° C.; 1H NMR δ 10.40 (s, 1H, CONH), 8.95 (d, J=2.4 Hz, 1H, H-2′), 8.61 (t, J=6.4 Hz, 1H, NHSO2), 8.42 (dd, J=2.5, 0.4 Hz, 1H, H-2″), 8.32 (dd, J=4.7, 1.4 Hz, 1H, H-6′), 8.21 (ddd, J=8.3, 2.5, 1.5 Hz, 1H, H-4′), 8.12 (dd, J=8.7, 2.5, 1H, H-6″), 7.90 (br d, J=8.3 Hz, 2H, H-2, H-6), 7.37-7.43 (m, 5H, H-3, H-5, H-3′″, H-5″), 7.25 (tt, J=7.4, 1.0 Hz, 1H, H-4″), 7.12-7.17 (m, 3H, H-5″, H-2′″, H-6″), 4.17 (d, J=6.4 Hz, 2H, CH2N); 13C NMR δ 165.4, 165.0, 152.9, 146.4, 144.5, 141.9, 141.4, 138.6, 135.8, 132.9, 132.1, 129.8 (2), 127.7 (2), 127.6 (2), 127.3, 125.3, 123.5, 121.5 (2), 111.5, 45.7; MS m/z 461.5 (MH+, 100%). Anal. calcd for C24H20N4O4: C, 62.60; H, 4.38; N, 12.17. Found: C, 62.48; H, 4.41; N, 12.14%.