Acetyl chloride → HCID 67261117, Verbindung

HRID 2359045Notizen

Reaktionsgleichung

[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[N:13]=3)=[CH:10][N:9]([CH:19]([CH3:21])[CH3:20])[N:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30].C1C[O:36][CH2:35][CH2:34]1>>[C:29]([N:18]([C:14]1[N:13]=[C:12]([C:11]2[C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)=[N:8][N:9]([CH:19]([CH3:21])[CH3:20])[CH:10]=2)[CH:17]=[CH:16][N:15]=1)[C:35](=[O:36])[CH3:34])(=[O:31])[CH3:30]

Komponenten

Edukt 4

HCID 6367Acetyl chloride

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 67260840HCID 67260840, Verbindung

Produkt 1

HCID 67261117HCID 67261117, VerbindungAusbeute 27 %

Versuchsvorschrift

To a solution of 4-[3-(5-chloro-2-thienyl)-1-isopropyl-1H-pyrazol-4-yl]pyrimidin-2-amine (1 eq, 1.9 mmol) and triethylamine (4 eq, 7.5 mmol) in 10 mL THF was added acetyl chloride (2 eq, 3.8 mmol). The mixture was then stirred at room temperature overnight and the solvent was evaporated. The residue was purified by chromatography on silica gel (heptane:ethyl acetate) to afford 220 mg of N-acetyl-N-{4-[3-(5-chloro-2-thienyl)-1-isopropyl-1H-pyrazol-4-yl]pyrimidin-2-yl}acetamide (27% yield).

Aufarbeitung

customthe solvent was evaporated
customThe residue was purified by chromatography on silica gel (heptane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-be5ebbd521524d8ca0ccf50e0af22f4b
Quelldatensatz: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08685974B2

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