9-(1-benzyl-4-methyl-1H-imidazol-2-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one → HCID 178430837, Verbindung

HRID 1467590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1467590
C([N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]1[CH:14]1[C:19]2=[N:20][NH:21][C:22](=[O:27])[C:23]3[CH:24]=[CH:25][CH:26]=[C:17]([C:18]=32)[NH:16][CH:15]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[CH3:13][C:11]1[N:10]=[C:9]([CH:14]2[C:19]3=[N:20][NH:21][C:22](=[O:27])[C:23]4[CH:24]=[CH:25][CH:26]=[C:17]([C:18]=43)[NH:16][CH:15]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[NH:8][CH:12]=1

Komponenten

4

Edukt 1

HCID 1363747039-(1-benzyl-4-methyl-1H-imidazol-2-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one

Produkt 1

HCID 178430837HCID 178430837, VerbindungAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 9-(1-benzyl-4-methyl-1H-imidazol-2-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (40 mg, 0.09 mmol) and palladium hydroxide on carbon catalyst (40 mg, 20% wt) in anhydrous methanol (15 mL) was purged with hydrogen (1 bar) at room temperature for 12 hr. The mixture was filtered and the filtrate was concentrated to give crude product, which was purified by pre-HPLC to give 9-(4-methyl-1H-imidazol-2-yl)-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (27 mg, yield 87%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 2.22 (dd, 3H), 4.77-4.86 (m, 2H), 7.06 (s, 1H), 7.20 (d, 1H), 7.36 (t, 5H), 7.55 (d, 1H), 7.62 (t, 1H); LC-MS (ESI) m/z: 3-(4 (M+1)+.

Aufarbeitung

  1. customwas purged with hydrogen (1 bar) at room temperature for 12 hr
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customto give crude product, which
  5. customwas purified by pre-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0b6eb826dac742b09065f2439e779a47
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999987B2

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