Acetyl chloride → HCID 86696385, Verbindung

HRID 870682Notizen

Reaktionsgleichung

C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:35])[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:25]4[N:26]=[C:27]([NH:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:28]=[CH:29][C:24]4=[N:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)(C)(C)C.C(Cl)(=[O:39])C>>[C:14]([OH:35])(=[O:39])[CH3:15].[NH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]([C:15]2[CH:16]=[CH:17][C:18]([C:21]3[N:25]4[N:26]=[C:27]([NH:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:28]=[CH:29][C:24]4=[N:23][CH:22]=3)=[CH:19][CH:20]=2)=[O:35])[CH2:12][CH2:13]1

Komponenten

Edukt 2

HCID 6367Acetyl chloride

HCID 86696384HCID 86696384, Verbindung

Produkt 1

HCID 86696385HCID 86696385, VerbindungAusbeute 150,3 %

Versuchsvorschrift

The solution of tert-butyl(1-(4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoyl)piperidin-4-yl)carbamate (47 mg, 0.1 mmol) was cooled to 0° C. and treated with acetyl chloride (225 mg, 2.86 mmol). The reaction was maintained at room temperature for overnight. The resulting solution was concentrated under reduced pressure and the residue was purified by preparative HPLC (neutral) to afford (4-aminopiperidin-1-yl)(4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)phenyl)methanone acetic acid salt (34 mg, 79% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 8.17-8.42 (m, J=8.3 Hz, 2H), 7.86 (s, 1H), 7.63 (d, J=9.6 Hz, 1H), 7.48-7.57 (m, J=8.6 Hz, 2H), 6.74 (d, J=9.6 Hz, 1H), 3.36-3.49 (m, 3H), 1.90-1.99 (m, 9H), 1.72 (quin, J=7.3 Hz, 2H), 1.63 (br. s., 2H), 1.44-1.55 (m, 2H), 1.01 (t, J=7.5 Hz, 3H); LRMS (ESI) m/e 393.2 [(M+H)+, calcd for C22H29N6O 393.2].

Aufarbeitung

concentrationThe resulting solution was concentrated under reduced pressure
customthe residue was purified by preparative HPLC (neutral)

Quellen und Nachweise

ORD-Eintrag: ord-3f2fee59eacb47249846b594d1b6d311
Quelldatensatz: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08969565B2

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