Sodium Hydroxide → 2-Ethyl-benzofuran-3-carboxylic acid [5-bromo-6-(1H-tetrazol-5-ylmethoxy)-naphthalen-2-ylmethyl]-methyl-amide

HRID 1357257Notes

Reaction equation

[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]#[N:15])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:31])[C:18]([C:20]1[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:21]=1[CH2:29][CH3:30])=[O:19])=[CH:7]2.[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[NH:34][N:33]=[N:32][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:31])[C:18]([C:20]1[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:21]=1[CH2:29][CH3:30])=[O:19])=[CH:7]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-ethyl-benzofuran-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (0.25 g, 0.5237 mmol), prepared in the previous step, sodium azide (0.10 g, 1.57 mmol) and ammonium chloride (0.084 g, 1.57 mmol) in 12 mL DMF was stirred under nitrogen at 100° C. for 5 h. The reaction was diluted with water, made basic with 1N NaOH and extracted four times with ethyl acetate. The combined organic extracts were acidified with 1N HCl, the solvent removed under reduced pressure and the resulting residue diluted with water. The solid foam that formed was collected by filtration and dried under reduced pressure to give the title compound (0.15 g, 56%) as a tan foam, MS m/z: 520 [M+H]+.

Workup

extractionextracted four times with ethyl acetate
customthe solvent removed under reduced pressure
additionthe resulting residue diluted with water
customThe solid foam that formed
filtrationwas collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-612cb19ac455486a94daeacf2a47f4e8
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06589970B2

Reaction notes

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