Acetyl chloride → HCID 86696387, Verbindung

HRID 870684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 870684
[CH2:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]3[CH:35]=[CH:34][C:18]([C:19]([N:21]4[CH2:26][CH2:25][N:24](C([O:29][C:30]([CH3:33])(C)C)=O)[CH2:23][CH2:22]4)=[O:20])=[CH:17][CH:16]=3)=[CH:13][N:14]=2)[N:11]=1)[CH2:2][CH2:3][CH3:4].C(Cl)(=[O:38])C>>[C:30]([OH:38])(=[O:29])[CH3:33].[CH2:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]3[CH:16]=[CH:17][C:18]([C:19]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[O:20])=[CH:34][CH:35]=3)=[CH:13][N:14]=2)[N:11]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

3

Edukt 2

HCID 6367Acetyl chlorideHCID 86696386HCID 86696386, Verbindung

Produkt 1

HCID 86696387HCID 86696387, VerbindungAusbeute 84,7 %

Versuchsvorschrift

The solution of tert-butyl 4-(4-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)benzoyl)piperazine-1-carboxylate (65 mg, 0.14 mmol) was cooled to 0° C. and treated with acetyl chloride (320 mg, 4.07 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-(6-(butylamino)imidazo[1,2-b]pyridazin-3-yl)phenyl)(piperazin-1-yl)methanone acetic acid salt (52 mg, 76% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 8.34 (d, J=8.3 Hz, 2H), 7.87 (s, 1H), 7.64 (d, J=9.6 Hz, 1H), 7.55 (d, J=8.3 Hz, 2H), 6.75 (d, J=9.6 Hz, 1H), 3.40 (t, J=7.2 Hz, 2H), 3.04 (br. s., 3H), 1.92-2.02 (m, 7H), 1.73 (t, J=7.2 Hz, 2H), 1.41-1.59 (m, 2H), 1.02 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 379.2 [(M+H)+, calcd for C21H27O 379.2].

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1120b7e6c03e4e37a96f3bdfa1584e03
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969565B2

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