Hydrochloric Acid → 5-((5-fluoropyridin-2-yl)methoxy)pyridazin-3(2H)-one

HRID 469684Notes

Reaction equation

HRID 469684 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[N:14][N:13](C3CCCCO3)[C:12](=[O:22])[CH:11]=2)=[N:6][CH:7]=1.Cl>CO.CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[N:14][NH:13][C:12](=[O:22])[CH:11]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 580921945-(5-Fluoro-pyridin-2-ylmethoxy)-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one

Product 1

HCID 580922585-((5-fluoropyridin-2-yl)methoxy)pyridazin-3(2H)-oneYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

5-((5-Fluoropyridin-2-yl)methoxy)-2-(tetrahydro-2H-pyran-2-yl)pyridazin-3(2H)-one (1.1 g, 3.6 mmol) was stirred in MeOH (5 mL) and 2 N HCl in Et2O (20 mL) was added. After 16 h, the mixture was diluted with Et2O (100 mL), and the solid was filtered off. The solid was stirred in NaHCO3 solution (15 mL) for 15 minutes and then refiltered to provide the title compound (620 mg, 78%) as a pink solid: 1H NMR (300 MHz, DMSO-d6) δ 12.69 (s, 1H), 8.60 (d, J=2.8 Hz, 1H), 7.85-7.78 (td, J=8.7, 2.9 Hz, 1H), 7.76 (d, J=2.7 Hz, 1H), 7.67-7.63 (dd, J=8.6, 4.5 Hz, 1H), 6.31 (s, 1H), 5.25 (s, 2H).

Workup

  1. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-ef5f428d3fd94d28a57902a3241e84f5
Source dataset
uspto-grants-2014_01
Patent number
US08629158B2

Reaction notes

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