Methyl Nicotinate → HCID 11992997, compound

HRID 2267155Notes

Reaction equation

[OH:1][NH:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[NH:4].[H-].[Na+].[C:20](OC)(=O)[C:21]1[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=1>O1CCCC1.C(OCC)(=O)C>[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:20]2[O:1][N:2]=[C:3]([N:5]3[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10]3)[N:4]=2)[CH:22]=1

Participants

Conditions

Temperature: 60 °C

Procedure

tert-Butyl 4-(N-hydroxyamidino)-piperazine-1-carboxylate (320 mg) prepared in Example 36 was dissolved in 3 ml of tetrahydrofuran, 36 mg of sodium hydride was added thereto, the mixture was stirred at 60° C. for 15 minutes, a solution of 360 mg of methyl nicotinate in 2 ml of tetrahydrofuran was added thereto and the mixture was heated to reflux for 1 hour. The reaction solution was diluted with ethyl acetate, washed with water and a saturated saline solution and dried over sodium sulfate. The residue prepared by evaporation of the solvent was purified by a preparative thin-layer silica gel chromatography (hexane:ethyl acetate=1:1) to give 39.7 mg of the title compound as a white solid.

Workup

temperaturethe mixture was heated
temperatureto reflux for 1 hour
washwashed with water
dry with materiala saturated saline solution and dried over sodium sulfate
customThe residue prepared by evaporation of the solvent
customwas purified by a preparative thin-layer silica gel chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-19d3ae553aa14252ac399710783c2270
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858800B2

Reaction notes

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