4-(Aminomethyl)-N-(pyridin-3-YL)benzamide → Benzamide

HRID 931469Notes

Reaction equation

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.N1N=C(S(Cl)(=O)=O)NC=1>N1C=CC=CC=1>[C:7]([NH2:9])(=[O:8])[C:6]1[CH:16]=[CH:17][CH:3]=[CH:4][CH:5]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 4-(aminomethyl)-N-(3-pyridinyl)benzamide (33) (295 mg, 1.3 mmol) and 4H-1,2,4-triazole-3-sulfonyl chloride (218 mg, 1.3 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 (0-25%) of MeOH/EtOAc, to give benzamide II-7 (176 mg, 38%) as a white powder: mp (MeOH/EtOAc) 266-269° C.; 1H NMR δ 14.79 (s, 1H, NH), 10.39 (s, 1H, CONH), 8.94 (d, J=2.2 Hz, 1H, H-2″), 8.78 (s, 1H, H-5′), 8.71 (br s, 1H, NHSO2), 8.31 (dd, J=4.7, 1.5 Hz, 1H, H-6″), 8.19 (ddd, J=8.3, 2.5, 1.5 Hz, 1H, H-4″), 7.93 (d, J=8.3 Hz, 2H, H-2, H-6), 7.46 (br d, J=8.3 Hz, 2H, H-3, H-5), 7.39 (dd, J=8.3, 4.7 Hz, 1H, H-5″), 4.30 (br d, J=4.7 Hz, 2H, CH2N); 13C NMR δ 165.6, 161.8, 145.7, 144.5, 142.0, 135.8, 133.1, 127.7 (2), 127.3 (2), 127.2, 123.5, 45.9, 1 resonance not observed; MS m/z 359.6 (MH+, 100%). Anal. calcd for C15H14N6O3S: C, 50.27; H, 3.94; N, 23.45. Found: C, 50.35; H, 3.82; N, 23.42%.

Workup

customThe solvent was evaporated
stirringthe residue stirred in ice/water (20 mL) for 1 h
filtrationThe precipitate was filtered
washwashed with water (5 mL)
customdried
customThe crude solid was purified by column chromatography
washeluting with a gradient (0-25%) of MeOH/EtOAc

Sources & evidence

ORD record: ord-4b5b7ee84b2f465eb08f1fbba32a6b19
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Reaction notes

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