N-(3,4-DiMethoxybenzyl)-2-fluoro-5-nitrobenzaMide → HCID 178491157, compound

HRID 1934679Notes

Reaction equation

F[C:2]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)=[O:5].[CH:25]([NH:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([NH2:34])[CH2:30][CH2:29]1)=[O:26]>N1C=CC=CC=1>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[O:14][CH3:15])[CH2:7][NH:6][C:4](=[O:5])[C:3]1[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[CH:21][C:2]=1[NH:34][C@H:31]1[CH2:32][CH2:33][C@H:28]([NH:27][CH:25]=[O:26])[CH2:29][CH2:30]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-fluoro-N-(3,4-dimethoxybenzyl)-5-nitrobenzamide (200 mg) and trans-4-formamidocyclohexylamine (170 mg) in pyridine (2 mL) was stirred for 4 hours at 50° C. The mixture was partitioned between ethyl acetate and water. The separated organic layer was washed with 1N HCl and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with 5% methanol in chloroform. The obtained product was recrystallized from acetone (2 mL) to give N-(3,4-dimethoxybenzyl)-2-[(trans-4-formamidocyclohexyl)amino]-5-nitrobenzamide as yellow crystals (164 mg).

Workup

customThe mixture was partitioned between ethyl acetate and water
washThe separated organic layer was washed with 1N HCl and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by a silica gel column chromatography
washeluting with 5% methanol in chloroform
customThe obtained product was recrystallized from acetone (2 mL)

Sources & evidence

ORD record: ord-0e40552e693045eea3133903dd127efb
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384080B1

Reaction notes

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