Triethylamine → 4-(3-(4-methoxypiperidine-1-carbonyl)benzyl)-5,7-dimethyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-one

HRID 1091735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091735
[CH3:1][C:2]1[NH:3][C:4]([CH3:22])=[C:5]2[C:10]=1[C:9]([CH2:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](O)=[O:16])=[N:8][NH:7][C:6]2=[O:21].[CH3:23][O:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C(N(CC)CC)C>CN(C=O)C>[CH3:23][O:24][CH:25]1[CH2:30][CH2:29][N:28]([C:15]([C:14]2[CH:13]=[C:12]([CH:20]=[CH:19][CH:18]=2)[CH2:11][C:9]2[C:10]3[C:5](=[C:4]([CH3:22])[NH:3][C:2]=3[CH3:1])[C:6](=[O:21])[NH:7][N:8]=2)=[O:16])[CH2:27][CH2:26]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 776664-MethoxypiperidineHCID 136101881HCID 136101881, Verbindung

Produkt 1

HCID 1363801884-(3-(4-methoxypiperidine-1-carbonyl)benzyl)-5,7-dimethyl-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-1-oneAusbeute 40,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(1H-Benzo[d][1,2,3]triazol-1-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.179 g, 0.47 mmol) was added to 3-((5,7-dimethyl-1-oxo-2,6-dihydro-1H-pyrrolo[3,4-d]pyridazin-4-yl)methyl)benzoic acid (51) (0.100 g, 0.34 mmol), 4-methoxypiperidine (0.043 g, 0.37 mmol) and triethylamine (0.117 mL, 0.84 mmol) in DMF (2 mL). The resulting solution was stirred at room temperature for 5 hours. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the desired compound (0.054 g, 40.9% yield). 1H NMR (400.132 MHz, DMSO) δ 1.18-1.93 (4H, m), 2.24 (3H, s), 2.51 (3H, s), 3.02-3.19 (2H, m), 3.25 (3H, s), 3.40 (2H, m), 3.76-3.97 (1H, m), 4.09 (2H, s), 7.14 (1H, s), 7.20 (1H, d), 7.27 (1H, d), 7.36 (1H, t), 11.08 (1H, s), 11.92 (1H, s); m/z (LC-MS, ESI+), RT=1.38 min (M+H=395.09).

Aufarbeitung

  1. customThe crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 19 mm diameter, 100 mm length)
  2. additionFractions containing the desired compound
  3. customwere evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-0754332cbe144e3e94fc985ac1714fd0
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129380B2

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