Hydrochloric Acid → 5-((6-(Trifluoromethyl)pyridin-3-yl)methoxy)pyridazin-3(2H)-one

HRID 474935Notes

Reaction equation

HRID 474935 reaction equation
O1CCCCC1[N:7]1[C:12](=[O:13])[CH:11]=[C:10]([O:14][CH2:15][C:16]2[CH:17]=[N:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=2)[CH:9]=[N:8]1.Cl>CO.CCOCC>[F:25][C:22]([F:23])([F:24])[C:19]1[N:18]=[CH:17][C:16]([CH2:15][O:14][C:10]2[CH:9]=[N:8][NH:7][C:12](=[O:13])[CH:11]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 668688942-(Tetrahydro-2H-pyran-2-yl)-5-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridazin-3(2H)-one

Product 1

HCID 668688325-((6-(Trifluoromethyl)pyridin-3-yl)methoxy)pyridazin-3(2H)-oneYield 67.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

2-(Tetrahydro-2H-pyran-2-yl)-5-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridazin-3(2H)-one (5.25 g, 12 mmol estimated) was stirred in MeOH (10 mL), and 2 N HCl in Et2O (50 mL) was added. After 16H, 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 (2.2 g, 67%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 12.74 (s, 1H), 8.78 (s, 1H), 8.20-8.16 (dd, J=8.1, 1.5 Hz, 1H), 8.00 (d, J=8.1 Hz, 1H), 7.76 (d, J=2.6 Hz, 1H), 6.31 (s, 1H), 5.25 (s, 2H).

Workup

  1. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-69a2aad1d20d4998a75d4ee92fae8caa
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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