3-Hydroxypyridine → HCID 57919248, compound

HRID 2381343Notes

Reaction equation

HRID 2381343 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=1.C[O:24][C:25](=[O:34])[CH:26](Br)[CH2:27][CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>>[CH:28]1([CH2:27][CH:26]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:22][C:18]3[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=3)[CH:6]=[N:5]2)[C:25]([OH:24])=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 3

HCID 79713-HydroxypyridineHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919248HCID 57919248, compoundYield 72%

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 pyridin-3-ol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[6-oxo-4-(pyridin-3-yloxy)-6H-pyridazin-1-yl]-propionic acid (10.5 g, 72%) as a solid; ESI-MS 330 [M+H+]; HPLC: >96% (purity). 1H-NMR (300 MHz, DMSO-d6): δ 1.11 (m, 2H), 1.52 (m, 7H), 2.01 (m, 1H), 2.22 (m, 1H), 5.32 (m, 1H), 5.89 (s, 1H), 7.56 (m, 1H), 7.84 (m, 1H), 8.15 (s, 1H), 8.59 (m, 2H), 13.00 (brs, 1H).

Sources & evidence

ORD record
ord-132a882b73ac42feb8845f1f48138195
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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