2-Methylpyridin-3-ol → HCID 57919190, compound

HRID 2381339Notes

Reaction equation

HRID 2381339 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[CH3:16][C:17]1[C:22]([OH:23])=[CH:21][CH:20]=[CH:19][N:18]=1.C[O:25][C:26](=[O:35])[CH:27](Br)[CH2:28][CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH:29]1([CH2:28][CH:27]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:23][C:22]3[C:17]([CH3:16])=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:6]=[N:5]2)[C:26]([OH:25])=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

4

Reactant 3

HCID 707192-Methylpyridin-3-olHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919190HCID 57919190, compoundYield 67%

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-methyl-pyridin-3-ol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2-methyl-pyridin-3-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (10.4 g, 67%) as a white solid; LC-MS 344 [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), purity>95% (214 nm). 1H-NMR (300 MHz, DMSO-d6) δ 13.01 (bs, 1H), 8.21 (s, 1H), 8.14 (s, 1H), 7.73 (m, 1H), 7.36 (m, 1H), 5.79 (s, 1H), 5.30 (m, 1H), 1.01-2.19 (m, 11H).

Sources & evidence

ORD record
ord-9e7f3a90f17f494b989dfc321ba06d7e
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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