Dimethylformamide → 2-[4-(2-acetyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid methyl ester

HRID 2381328Notes

Reaction equation

[H-].[Na+].[C:3]([C:6]1[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=1[O:8][C:9]1[CH:14]=[N:13][NH:12][C:11](=[O:15])[CH:10]=1)(=[O:5])[CH3:4].CN(C)C=O.[CH3:25][O:26][C:27](=[O:36])[CH:28](Br)[CH2:29][CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>O1CCCC1>[CH3:25][O:26][C:27](=[O:36])[CH:28]([N:12]1[C:11](=[O:15])[CH:10]=[C:9]([O:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=2[C:3](=[O:5])[CH3:4])[CH:14]=[N:13]1)[CH2:29][CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride in mineral oil (3.65 g) was added to a solution of 5-(2-acetyl-phenoxy)-2H-pyridazin-3-one (16.3 g, 0.07 mol) in tetrahydrofuran (340 mL) at 0° C. The resulting mixture was stirred at 0° C. for 10 min and then was warmed to 20° C., where it stirred for 50 min. After this time, N,N-dimethylformamide (45 mL) and 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10, 25 g, 0.11 mol) were added to the reaction. The reaction was then warmed to 50° C. overnight. After this time, the reaction was concentrated in vacuo. Silica gel column chromatography afforded 2-[4-(2-acetyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid methyl ester (23.4 g, 86%); ESI-MS 385 [M+H+].

Workup

temperaturewas warmed to 20° C.
stirringwhere it stirred for 50 min
temperatureThe reaction was then warmed to 50° C. overnight
concentrationAfter this time, the reaction was concentrated in vacuo

Sources & evidence

ORD record: ord-a0004e6fd79c462893b2a01221e4f9f8
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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