Hydrochloric Acid → HCID 52992014, compound

Reaction equation

[N:1]1[NH:2][C:3](=[O:7])[CH:4]=[CH:5][CH:6]=1.[OH-].[Na+].Br[C@@H:11]([CH3:15])[C:12]([OH:14])=[O:13].Cl>>[O:7]=[C:3]1[N:2]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])[N:1]=[CH:6][CH:5]=[CH:4]1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 681533(2H)-Pyridazinone

HCID 6422322-Bromopropionic acid, (S)-

Product 1

HCID 52992014HCID 52992014, compound

Conditions

Temperature: 90 °C

Procedure

To 3(2H)-pyridazinone (1.19 g, 12.3 mmol) was added 5 N sodium hydroxide solution (4.9 ml) followed by (2S)-2-bromopropanoic acid (1.11 ml, 12.3 mmol). The reaction mixture was heated at 90° C. for 1 h. After cooled downed to ambient temperature, 2 N hydrochloric acid (6.2 ml) was added and the reaction mixture was directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). The pure fractions were collected and the solvent was removed in vacuo to afford the title compound as pale yellow solid. 2-[6-Oxopyridazin-1(6H)-yl]propanoic acid: 1H NMR (D2O): δ 8.07 (dd, J=4.1, 1.6 Hz, 1H), 7.53 (dd, 9.3, 3.9 Hz, 1H), 7.09 (dd, J=9.4, 1.6 Hz, 1H), 5.46 (m, 1H), 1.64 (d, J=7.3 Hz, 3H).