Dimethylamine → HCID 68525892, compound

HRID 1932444Notes

Reaction equation

Cl[CH2:2][C:3]([N:5]([C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][N:33]=2)=[CH:27][CH:26]=1)[CH2:6][C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:24]=[CH:23][C:22]3[O:21][CH2:20][O:19][C:18]=3[CH:17]=2)[CH2:11][CH2:10]1)=[O:8])=[O:4].[CH3:41][NH:42][CH3:43].O>C(#N)C>[CH3:41][N:42]([CH3:43])[CH2:2][C:3]([N:5]([C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][N:33]=2)=[CH:27][CH:26]=1)[CH2:6][C:7]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:24]=[CH:23][C:22]3[O:21][CH2:20][O:19][C:18]=3[CH:17]=2)[CH2:11][CH2:10]1)=[O:8])=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-chloro-N-[4-(5-nitropyridin-2-yloxy)phenyl]-N-[2-(4-piperonylpiperazin-1-yl)-2-oxoethyl]acetamide (0.300 g, 0.528 mmol) in acetonitrile (3 mL) was added at room temperature dimethylamine (0.150 mL, 1.63 mmol), and the resulting solution was stirred for 2 hours at 50° C. Water was added to the reaction mixture, and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, evaporated, and the residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1), to thereby yield 0.270 g of the title compound.

Workup

extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
customevaporated
customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1)

Sources & evidence

ORD record: ord-a1afb1108ca04a7680753fa136f333c1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188277B2

Reaction notes

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