Acetic Acid → HCID 178518345, Verbindung

HRID 2236807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2236807
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])/[C:5]/2=[CH:14]\[NH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:42]1(=O)[CH2:45][CH2:44][CH2:43]1.C(O)(=O)C.C(=O)(O)[O-].[Na+]>CN1CCCC1=O.C(Cl)Cl>[CH:42]1([N:25]2[CH2:24][CH2:23][N:22]([C:19]3[CH:18]=[CH:17][C:16]([NH:15]/[CH:14]=[C:5]4\[C:6](=[O:13])[NH:7][C:8](=[O:12])[C:9]5[C:4]\4=[CH:3][C:2]([I:1])=[CH:11][CH:10]=5)=[CH:21][CH:20]=3)[CH2:27][CH2:26]2)[CH2:45][CH2:44][CH2:43]1

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 14496CyclobutanoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178518347HCID 178518347, Verbindung

Produkt 1

HCID 178518345HCID 178518345, VerbindungAusbeute 60,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

(4Z)-6-Iodo-4-{[(4-piperazin-1-ylphenyl)amino]methylene}isoquinoline-1,3(2H,4H)-dione (47.4 mg, 0.1 mmol) is dissolved in N-methylpyrrolidinone (1 mL) and methylene chloride (0.3 mL), followed by addition of sodium triacetoxyborohydride (244 mg, 1.15 mmol), cyclobutanone (0.195 mL, 2.58 mmol) and acetic acid (0.15 mL, 2.6 mmol). After stirring at room temperature for 40 min, methylene chloride and saturated sodium bicarbonate solution were added. The organic layer is separated and dried to give 32 mg (60%) of the title compound as a yellow solid. MS (ESI) m/z 529.4 (M+H)+1.

Aufarbeitung

  1. customThe organic layer is separated
  2. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fec3dfc98a684ead8ae6c3bd94ae0fc9
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713994B2

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