2-(Piperidin-1-yl)phenol → HCID 57919185, compound

HRID 2381341Notes

Reaction equation

HRID 2381341 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[N:16]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[OH:28])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C[O:30][C:31](=[O:40])[CH:32](Br)[CH2:33][CH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>>[CH:34]1([CH2:33][CH:32]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:28][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:6]=[N:5]2)[C:31]([OH:30])=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

4

Reactant 3

HCID 32622502-(Piperidin-1-yl)phenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919185HCID 57919185, compoundYield 97%

Procedure

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 2-(piperidin-1-yl)phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[6-oxo-4-(2-piperidin-1-yl-phenoxy)-6H-pyridazin-1-yl]-propionic acid (3.3 g, 97%) as a white solid; ESI-MS 412 [M+H+]; HPLC conditions (0.17% trifluoroacetic acid in acetonitrile/water, 50%-100% acetonitrile, gradient, 1 mL/min, Venusil MP-C18, C18-15 cm×4.6 mm-5 μm), purity>98%. 1H-NMR (300 MHz, CDCl3) δ 7.78 (s, 1H), 7.08 (m, 4H), 5.99 (s, 1H), 5.52 (m, 1H), 2.93 (m, 4H), 2.35 (m, 1H), 2.12 (m, 1H), 1.60 (m, 13H), 1.16 (m, 2H).

Sources & evidence

ORD record
ord-bdcc0b6a11b64a1dacdcf86da22517eb
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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