Hydrochloric Acid → HCID 57919322, compound

HRID 2381387Notes

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

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-cyclopentyl-2-{4-[2-(2-hydroxy-ethyl)-phenoxy]-6-oxo-6H-pyridazin-1-yl}-propionic acid methyl ester (386 mg, 1 mmol) in dioxane (5 mL) was treated with a 6N aqueous hydrochloric acid solution (5 mL). The reaction solution was stirred at 25° C. overnight and then concentrated in vacuo. Chromatography afforded 3-cyclopentyl-2-{4-[2-(2-hydroxy-ethyl)-phenoxy]-6-oxo-6H-pyridazin-1-yl}-propionic acid (156 mg, 42%); LC-MS: 373 (M+1)+, tR=3.28 min. Purity on HPLC: tR=5.98 min, 97.9% (214 nm), 96.5% (254 nm). 1H NMR (300 MHz, DMSO-d6): δ12.95 (s, 1H, broad), 8.14 (s, 1H), 7.46-7.20 (m, 4H), 6.37 (d, 1H, J=2.7 Hz), 5.31 (dd, 1H, J=10.5 Hz, J=4.5 Hz), 4.70 (t, 1H, J=5.4 Hz), 3.59-3.52 (m, 2H), 3.66 (t, J=6.6 Hz, 1H), 2.17-1.97 (m, 2H), 1.58-1.01 (m, 9H).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-df48e37ede5947c684ef3dcccca49d81
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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