Potassium Carbonate → HCID 57919278, compound

HRID 2381347Notes

Reaction equation

[Cl:1][C:2]1[C:3](=[O:15])[N:4]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[N:5]=[CH:6][C:7]=1Cl.C(=O)([O-])[O-].[K+].[K+].[OH:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[C:25]#[N:26]>C(#N)C>[Cl:1][C:2]1[C:3](=[O:15])[N:4]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[N:5]=[CH:6][C:7]=1[O:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[C:25]#[N:26]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4,5-dichloro-2-(tetrahydropyran-2-yl)-2H-pyridazin-3-one (Intermediate 20, 60 g, 0.24 mol) in acetonitrile (500 mL) was treated with potassium carbonate (35.2 g, 0.26 mol) and 2-hydroxy-benzonitrile (29 g, 0.24 mol). The resulting reaction mixture was heated at reflux for 2 h and then allowed to cool to 25° C. The reaction mixture was then partitioned between water and methylene chloride. The organics were washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, rinsed, and concentrated in vacuo to afford 2-[5-chloro-6-oxo-1-(tetrahydro-pyran-2-yl)-1,6-dihydro-pyridazin-4-yloxy]-benzonitrile (79 g, 99%); ESI-MS 332 [M+H+]; HPLC: >99% (purity). 1H-NMR (300 MHz, CDCl3) δ 7.74-7.76 (m, 1H), 7.58-7.64 (m, 2H), 7.31-7.34 (m, 1H), 6.07-6.10 (d, 1H), 4.12-4.16 (d, 1H), 3.73-3.80 (t, 1H), 2.15-1.60 (m, 6H).

Workup

customThe resulting reaction mixture
temperaturewas heated
temperatureat reflux for 2 h
customThe reaction mixture was then partitioned between water and methylene chloride
washThe organics were washed with a saturated aqueous sodium chloride solution
dry with materialdried over sodium sulfate
filtrationfiltered
washrinsed
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f23acce2c10a47e5bdafaf61ea76d4dd
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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