Potassium Hydroxide → HCID 58945820, compound

HRID 2267146Notes

Reaction equation

[NH:1]1[CH:5]=[C:4]([C:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH:11]=2)[N:3]=[N:2]1.Cl[C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1.[OH-].[K+].[H-].[Na+]>CN(C)C=O.O>[N:21]1[CH:22]=[CH:23][N:24]=[CH:25][C:20]=1[N:1]1[CH:5]=[C:4]([C:6]2[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH:11]=2)[N:3]=[N:2]1

Participants

Conditions

Temperature: 120 °C

Procedure

tert-butyl 4-(1H-[1,2,3]triazol-4-yl)-1,2,3,6-tetra-hydropyridine-1-carboxylate (10 mg) prepared in the above 3) was dissolved in 1 ml of N,N-dimethylformamide, 0.04 ml of 2-chloropyrazine, 11 mg of powdery potassium hydroxide and 10 mg of sodium hydride were added thereto and the mixture was stirred for 5 hours under heating at 120° C. The reaction solution was allowed to cool down to room temperature, water was added thereto, the mixture was extracted with ethyl acetate, the extract was dried over sodium sulfate and the solvent was evaporated in vacuo. The resulting residue was separated and purified by a thin-layer chromatography (ethyl acetate/hexane=1/2) to give 4.5 mg of the title compound as a white solid.

Workup

temperatureto cool down to room temperature
extractionthe mixture was extracted with ethyl acetate
dry with materialthe extract was dried over sodium sulfate
customthe solvent was evaporated in vacuo
customThe resulting residue was separated
custompurified by a thin-layer chromatography (ethyl acetate/hexane=1/2)

Sources & evidence

ORD record: ord-c5a4e462108d49c0a6679f033f031d4c
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858800B2

Reaction notes

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