Sodium hydride → HCID 131730788, compound

HRID 80944

Reaction equation

[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[N:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[H-].[Na+].[Cl:25][CH2:26][C:27]([N:29]([CH3:31])[CH3:30])=[O:28]>CN(C=O)C>[ClH:25].[ClH:25].[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:15]=[N:14][C:13]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:26][C:27]([N:29]([CH3:31])[CH3:30])=[O:28])=[CH:20][CH:21]=3)=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 4-[6-(4-isopropyl-piperazin-1-yl)-pyridazin-3-yl]-phenol (110 mg, 0.37 mmol) and 60% sodium hydride (58 mg, 1.45 mmol) in dry DMF (5 mL) was heated at 60° C. for 30 min. 2-Chloro-N,N-dimethylacetamide (54 mg, 0.44 mmol) was added and heating at 60° C. was continued for another 20 h. The reaction mixture was evaporated to dryness and partitioned between water (10 mL) and DCM (10 mL). The organic phase was isolated, washed with brine (5 mL), dried over anhydrous magnesium sulphate, and evaporated to dryness in vacuo. The residue was dissolved in hot ethyl acetate and HClg in Et2O was added to give the title compound.

Workup

temperatureheating at 60° C.
customThe reaction mixture was evaporated to dryness
custompartitioned between water (10 mL) and DCM (10 mL)
customThe organic phase was isolated
washwashed with brine (5 mL)
dry with materialdried over anhydrous magnesium sulphate
customevaporated to dryness in vacuo
dissolutionThe residue was dissolved in hot ethyl acetate
additionHClg in Et2O was added

Sources & evidence

ORD record: ord-ad58286448e340c4add39b118395f36f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846677B2

Linked notes

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