تفاعل #1018647

معادلة التفاعل

4-(aminomethyl)-N-(3-pyridinyl)benzamide

4-(Aminomethyl)-N-(3-pyridinyl)benzamide

6-phenoxy-3-pyridinesulfonyl chloride

→

benzamide

المذيبات

pyridine

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was evaporated
2. 2
   workup.STIRRINGthe residue stirred in ice/water (20 mL) for 1 h
3. 3
   ترشيحThe precipitate was filtered
4. 4
   غسيلwashed with water (5 mL)
5. 5
   أخرىdried
6. 6
   أخرىThe crude solid was purified by column chromatography
7. 7
   غسيلeluting with a gradient (0-20%) of MeOH/EtOAc

الإجراء التجريبي

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%.

المصدر