1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 89726458, Verbindung

HRID 1777726Notizen

Reaktionsgleichung

Br[C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C1CCN2C(=NCCC2)CC1>CC#N.CC(=O)OCC.O>[C:14]([O:13][C:11]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[S:6][CH:5]=[N:4][C:3]=2[C:7]([O:9][CH3:10])=[O:8])[CH2:20][CH2:19]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of methyl 5-bromo-1,3-thiazole-4-carboxylate (10 g) in MeCN (120 mL) was added 1-Boc-piperazine (8.56 g) followed by DBU (10.1 mL). The resulting solution was stirred at 80° C. for 5 h. The reaction mixture was diluted with EA and water. The layers were separated and the org. phase was further washed with water. The combined aq. layers were extracted with EA. The combined org. layers were dried over Na2SO4, filtrated off and evaporated in vacuo. The crude was purified by CC (Biotage, SNAP 100 g cartridge, solvent A: Hept; solvent B: EA; gradient in % B: 10 for 2CV, 10 to 50 over 12CV, 50 for 3CV) to afford 7.65 g of yellow oil. LC-MS (B): tR=0.79 min; [M+H]+: 328.37.

Aufarbeitung

customThe layers were separated
washphase was further washed with water
extractionThe combined aq. layers were extracted with EA
dry with materiallayers were dried over Na2SO4
filtrationfiltrated off
customevaporated in vacuo
customThe crude was purified by CC (Biotage, SNAP 100 g cartridge, solvent A: Hept; solvent B: EA; gradient in % B: 10 for 2CV, 10 to 50 over 12CV, 50 for 3CV)

Quellen und Nachweise

ORD-Eintrag: ord-b1ab0fff90eb4fd1ad6510d135cd6a0d
Quelldatensatz: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09266876B2

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