7-Methylindan-4-ol → HCID 57919301, Verbindung

HRID 2381373

Reaktionsgleichung

Reaktionsgleichung von HRID 2381373
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[CH3:16][C:17]1[C:25]2[CH2:24][CH2:23][CH2:22][C:21]=2[C:20]([OH:26])=[CH:19][CH:18]=1.C[O:28][C:29](=[O:38])[CH:30](Br)[CH2:31][CH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH:32]1([CH2:31][CH:30]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:26][C:20]3[CH:19]=[CH:18][C:17]([CH3:16])=[C:25]4[C:21]=3[CH2:22][CH2:23][CH2:24]4)[CH:6]=[N:5]2)[C:29]([OH:28])=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33]1

Komponenten

4

Edukt 3

HCID 853987-Methylindan-4-olHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Produkt 1

HCID 57919301HCID 57919301, Verbindung

Versuchsvorschrift

In an analogous manner to the stepwise sequence outlined in intermediate 19, starting from 4,5-dichloro-2-(tetrahydropyran-2-yl)-2H-pyridazin-3-one (Intermediate 20) and 7-methyl-indan-4-ol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(7-methyl-indan-4-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (10 g, 86% for the final step); LC-MS: 383 [M+1]+, tR=3.77 min. HPLC: 97.75% at 214 nm, 98.81% at 254 nm, tR=7.98 min. 1H NMR (300 MHz, CDCl3): δ 7.85 (d, 1H, J=2.4 Hz), 7.01 (d, 1H, J=8.1 Hz), 6.77 (d, 1H, J=8.1 Hz), 5.88 (d, 1H, J=2.4 Hz), 5.49 (dd, 1H, J1=10.2 Hz, J2=4.8 Hz), 2.87 (t, 2H, J=7.5 Hz), 2.77 (t, 2H, J=7.5 Hz), 2.26 (s, 3H), 2.15˜2.07 (m, 2H), 1.80˜1.49 (m, 7H), 1.25˜1.14 (m, 4H).

Quellen und Nachweise

ORD-Eintrag
ord-df7ca462e77b4ec68df46d92362fccdc
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258134B2

Verknüpfte Notizen

Wird geladen…