1,2-dimethyl-1H-imidazole-5-sulfonyl chloride → Benzamide

HRID 931468Notes

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.CN1C(S(Cl)(=O)=O)=CN=C1C>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) (341 mg, 1.5 mmol) and 1,2-dimethyl-1H-imidazole-5-sulfonyl chloride (292 mg, 1.5 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-6 (201 mg, 35%) as a white powder: mp (MeOH/EtOAc) 238-240° C.; 1H NMR δ 10.37 (s, 1H, CONH), 8.92 (br s, 1H, H-2′), 8.31 (dd, J=4.7, 1.5 Hz, 1H, H-6′), 8.18 (ddd, J=8.3, 2.5, 1.5 Hz, 1H, H-4′), 7.97 (br s, 1H, NHSO2), 7.91 (br dd, J=8.3, 1.7 Hz, 2H, H-2, H-6), 7.61 (s, 1H, H-5″), 7.44 (br d, J=8.3 Hz, 2H, H-3, H-5), 7.39 (ddd, J=8.3, 4.6, 0.6 Hz, 1H, H-5′), 4.10 (br d, J=6.0 Hz, 2H, CH2N), 3.58 (s, 3H, NCH3), 2.30 (s, 3H, CH3); 13C NMR δ 165.7, 146.4, 144.5, 142.5, 142.0, 137.1, 135.8, 132.9, 127.5 (2), 127.4 (2), 127.3, 124.7, 123.5, 45.7, 32.8, 12.4; MS m/z 386.6 (MH+, 100%). Anal. calcd for C18H19N5O3S: C, 56.09; H, 4.97; N, 18.17. Found: C, 56.15; H, 5.08; N, 18.00%.

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 (0-20%) of MeOH/EtOAc

Sources & evidence

ORD record: ord-12b83287ccaa475092ce61f583474df9
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296732B2

Reaction notes

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