Dimethylamine → 2-(2-(4-((dimethylamino)methyl)-2-methylphenyl)-2-oxoethyl)-5-((5-methoxypyridin-2-yl)methoxy)pyridazin-3(2H)-one

HRID 1425772Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:28])[CH2:10][N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][N:21]=3)[CH:13]=[N:12]2)=[C:5]([CH3:29])[CH:4]=1.[CH3:30][NH:31][CH3:32]>CN(C)C(=O)C>[CH3:30][N:31]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:28])[CH2:10][N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][N:21]=3)[CH:13]=[N:12]2)=[C:5]([CH3:29])[CH:4]=1)[CH3:32]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2-[2-(4-Bromomethyl-2-methyl-phenyl)-2-oxo-ethyl]-5-(5-methoxy-pyridin-2-ylmethoxy)-2H-pyridazin-3-one (preparation 9d, 120 mg, 0.26 mmol) in N,N-dimethylacetamide (2 mL) is added dimethylamine (0.76 mmol, 2 M solution in THF). The reaction mixture is stirred for 4 h at 40° C. The mixture is purified via reverse phase HPLC chromatography (Waters XBridge 5 μm, gradient 5%→90% acetonitrile in water+0.3% NH4OH, 120 mL/min).

Workup

customThe mixture is purified via reverse phase HPLC chromatography (Waters XBridge 5 μm, gradient 5%→90% acetonitrile in water+0.3% NH4OH, 120 mL/min)

Sources & evidence

ORD record: ord-c2bd9a3a4c0b4f09b844483782243cd9
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933079B2

Reaction notes

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