Diethylamine → HCID 86612229, compound

HRID 30015Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH:9][CH2:10][CH3:11])[CH3:8].[Cl:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=2)[C:16]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31]Cl)=[CH:27][CH:26]=2)=[N:15][N:14]=1>C(O)C>[Cl:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=2)[C:16]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][N:9]([CH2:10][CH3:11])[CH2:7][CH3:8])=[CH:27][CH:26]=2)=[N:15][N:14]=1

Participants

Conditions

Temperature: 85 °C

Procedure

280 mg (2 mmol) of potassium carbonate and 0.3 mL of diethylamine are added to a solution of 319 mg (1 mmol) of 1-chloro-4-(4-chloromethylphenyl)-7-methoxyphthalazine (synthesized in 30.3) in 3 mL of ethanol. The mixture is stirred at 85° C. for 4 hours. The ethanol is evaporated off and the residue is taken up in water and extracted with dichloromethane. The organic extracts are washed with brine, dried over anhydrous sodium sulfate and then evaporated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel (solvent: 95/5 to 85/15 (v/v) dichloromethane/methanol). 287 mg of product are obtained (80% yield).

Workup

customThe ethanol is evaporated off
extractionextracted with dichloromethane
washThe organic extracts are washed with brine
dry with materialdried over anhydrous sodium sulfate
customevaporated under reduced pressure
customThe residue obtained
customis purified by chromatography on a column of silica gel (solvent: 95/5 to 85/15 (v/v) dichloromethane/methanol)

Sources & evidence

ORD record: ord-cd90850b3e2f4158a1ed82648e78d21c
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423030B2

Reaction notes

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