1-Naphthol → HCID 57919189, compound

HRID 2381323Notes

Reaction equation

HRID 2381323 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[C:16]1([OH:26])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=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:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:18][CH:17]=3)[CH:6]=[N:5]2)[C:29]([OH:28])=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

4

Reactant 3

HCID 70051-NaphtholHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919189HCID 57919189, compoundYield 80%

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 naphthalen-1-ol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(naphthalen-1-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (9.1 g, 80%) as a solid; ESI-MS 379 [M+H+]; HPLC (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), >96% (purity). 1H-NMR (300 MHz, CDCl3) δ 8.22-8.21 (d, 1H), 8.05-7.91 (m, 3H), 7.65-7.58 (m, 3H), 7.42-7.39 (d, 1H), 5.78-5.77 (t, 1H), 5.53-5.48 (m, 1H), 2.45-2.35 (m, 1H), 2.17-2.04 (m, 1H), 1.85-1.14 (m, 9H).

Sources & evidence

ORD record
ord-36a6a02d415e4d77b0d51a5155e3e09b
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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