2-Cyclopentylphenol → HCID 57919158, compound

HRID 2381321Notes

Reaction equation

HRID 2381321 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[CH:16]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[OH:27])[CH2:20][CH2:19][CH2:18][CH2:17]1.C[O:29][C:30](=[O:39])[CH:31](Br)[CH2:32][CH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>>[CH:33]1([CH2:32][CH:31]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:27][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[CH:6]=[N:5]2)[C:30]([OH:29])=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

4

Reactant 3

HCID 802852-CyclopentylphenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919158HCID 57919158, compoundYield 88%

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-cyclopentyl-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2-cyclopentyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (12.89 g, 88%) as a white solid; LC-MS [M+H+]=397; HPLC (0.1% trifluoroacetic acid in acetonitrile/water, 50%-100% acetonitrile, gradient, 1 mL/min, Venusil MP-C18, C18-150 cm×4.6 mm-5 μm), 214 nm, 97.39%, 254 nm, 96.72%. 1H-NMR (300 MHz, CDCl3) δ 7.88 (s, 1H), 7.29-7.41 (m, 1H), 7.22-7.26 (m, 2H), 6.98-7.01 (m, 1H), 5.91-5.92 (d, J=3, 1H), 5.49-5.54 (m, 1H), 3.03-3.12 (m, 1H), 2.28-2.38 (m, 1H), 2.09-2.18 (m, 1H), 1.95-1.98 (d, J=9 Hz, 2H), 1.50-1.79 (m, 13H), 1.09-1.26 (m, 2H).

Sources & evidence

ORD record
ord-09ca7422ea6341bba4e58c7be2d5ed3e
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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