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

HRID 2381329Notes

Reaction equation

C[O:2][C:3](=[O:28])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[C:14]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25](=[O:27])[CH3:26])[CH:13]=[N:12]1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1>O1CCOCC1.Cl>[C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:18][C:14]1[CH:13]=[N:12][N:11]([CH:4]([CH2:5][CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[C:3]([OH:28])=[O:2])[C:16](=[O:17])[CH:15]=1)(=[O:27])[CH3:26]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 2-[4-(2-acetyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid methyl ester (23.4 g, 0.061 mol) in 1,4-dioxane (230 mL) and hydrochloric acid (230 mL) was stirred at reflux overnight. After this time, the reaction was cooled to 25° C., concentrated in vacuo, and was treated with acetone (200 mL) and stirred at 25° C. for 1 h. The resulting precipitate was collected by filtration, washed with petroleum ether, acetone, ethyl acetate, and then dried to afford 2-[4-(2-acetyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid (12 g, 53%); ESI-MS 371 [M+H+]; HPLC: >98% (purity). 1H-NMR (300 MHz, DMSO-d6) δ 1.14 (m, 2H), 1.45 (m, 7H), 1.98 (m, 1H), 2.02 (m, 1H); 5.34 (m, 1H); 5.77 (s, 1H); 7.43 (m, 1H); 7.54 (m, 1H); 7.76 (m, 1H); 7.95 (m, 1H); 8.13 (m, 1H) 13.01 (s, 1H).

Workup

temperatureat reflux overnight
concentrationconcentrated in vacuo
additionwas treated with acetone (200 mL)
filtrationThe resulting precipitate was collected by filtration
washwashed with petroleum ether, acetone, ethyl acetate
customdried

Sources & evidence

ORD record: ord-8e0b311e549b48408a91f5bc1ec4d270
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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