2-Methanesulfonylphenol → 3-cyclopentyl-2-[4-(2-methanesulfonyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid

HRID 2381337Notes

Reaction equation

HRID 2381337 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[OH:26])(=[O:19])=[O:18].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:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:17]([CH3:16])(=[O:18])=[O:19])[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 5989982-MethanesulfonylphenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 579191503-cyclopentyl-2-[4-(2-methanesulfonyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acidYield 68%

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-methanesulfonyl-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2-methanesulfonyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (15 g, 68%) as a white solid; LC-MS: [M+H+]=407; 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), purity 98%. 1H-NMR (300 MHz, DMSO-d6) δ 1.42 (m, 2H), 1.55 (m, 7H), 1.57 (s, 1H), 1.59 (s, 1H), 3.31 (s, 1H), 5.31 (m, 1H), 7.63 (m, 1H), 7.87 (s, 2H), 7.98 (m, 1H), 8.19 (s, 1H).

Sources & evidence

ORD record
ord-b83d48c3a0834f65a82403d2321848c6
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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