Methyl iodide → [5-(2,2,4-Trimethyl-piperazin-1-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 2391860

Reaktionsgleichung

CI.[C:3]([O:7][C:8](=[O:25])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:22][CH2:21][NH:20][CH2:19][C:18]2([CH3:24])[CH3:23])=[CH:12][N:11]=1)([CH3:6])([CH3:5])[CH3:4].[C:26](=O)([O-])[O-].[K+].[K+]>COCCOC>[C:3]([O:7][C:8](=[O:25])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH3:26])[CH2:19][C:18]2([CH3:24])[CH3:23])=[CH:12][N:11]=1)([CH3:6])([CH3:4])[CH3:5]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

Methyl iodide (954 μL, 15.3 mmol, 1.3 equiv) was added dropwise to a suspension of [5-(2,2-dimethyl-piperazin-1-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (Step 109.3) (3.8 g, 11.8 mmol) and potassium carbonate (2.13 g, 15.4 mmol, 1.3 equiv) in DME (25 mL). The reaction mixture was heated to 50° C., stirred for 2 h, allowed to cool, quenched by addition of a H2O and extracted with DCM. The organic layer was washed with a saturated aqueous solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 98:1:1) to afford 1.94 g of the title compound as an off-white solid. Title compound: ESI-MS: 335.3 [M+H]+; TLC: Rf=0.31 (DCM/MeOH, 9:1).

Aufarbeitung

temperatureto cool
customquenched by addition of a H2O
extractionextracted with DCM
washThe organic layer was washed with a saturated aqueous solution of NaHCO3
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 98:1:1)

Quellen und Nachweise

ORD-Eintrag: ord-fbd1bf5ee55643f5bdea59cc69dc1629
Quelldatensatz: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08273882B2

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