Water → HCID 54122729, compound

HRID 1650194Notes

Reaction equation

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

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of 5-amino-l,2,3-triazole-4-carboxamide (182 mg, 1.43 mmol) in 5 ml of dry dimethylformamide (DMF) is treated with 50% sodium hydride dispersion in mineral oil (70mg). The reaction mixture is warmed to 45° C. and stirred for 1 hour. To this mixture, a solution of 4-(1-naphthoyl)-3,5dimethylbenzyl bromide (0.43 g, 1.2 mmol) in 5 ml of dry DMF is added. The reaction mixture is stirred at 45° C. for an additional 20 minutes and then stirred at room temperature for 1 hour. The reaction mixture is added slowly to water containing a small quantity of glacial acetic acid. The mixture is extracted with methylene chloride and the combined extracts washed with brine and dried with anhydrous sodium sulfate. Solvent is removed and the crude mixture of two triazoles is chromatographed on silica gel to give the titled compound.

Workup

stirringThe reaction mixture is stirred at 45° C. for an additional 20 minutes
stirringstirred at room temperature for 1 hour
extractionThe mixture is extracted with methylene chloride
washthe combined extracts washed with brine
dry with materialdried with anhydrous sodium sulfate
customSolvent is removed
additionthe crude mixture of two triazoles
customis chromatographed on silica gel

Sources & evidence

ORD record: ord-54c968cd881d431eb09abeb0e15c1a97
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04923885

Reaction notes

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