Sodium Bicarbonate → HCID 18681037, compound

HRID 276022Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:21])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[C:12]([NH2:20])[CH:11]=1.Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:31]=[N:32][S:33][CH:34]=2)=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:21])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[C:12]([NH:20][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[N:31]=[N:32][S:33][CH:34]=3)=[CH:26][CH:25]=2)[CH:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 0.800 g of N-(2-pyridylmethyl)-4-acetylamino-3-aminobenzamide in 10 ml of methanol were added 1.08 g of 4-(4-bromomethylphenyl)-1,2,3-thiadiazole and 0.710 g of sodium hydrogencarbonate, and the mixture was stirred at 70° C. for 1 hour. The reaction solution was concentrated, and was purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and methanol at a ratio of 9:1) to give 0.830 g of N-(2-pyridylmethyl)-4-acetylamino-3-[4-(1,2,3-thiadiazol-4-yl)benzylamino]benzamide

Workup

concentrationThe reaction solution was concentrated
customwas purified through silica-gel column chromatography (eluent
additiona mixture of ethyl acetate and methanol at a ratio of 9:1)

Sources & evidence

ORD record: ord-5d09389d2a044361a003890b8b35a5fd
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352985B1

Reaction notes

Loading…