1,5-Dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid [2-benzylamino-4-(4-methyl-piperazin-1-yl)-phenyl]-amide → 5-[1-Benzyl-6-(4-methylpiperazin-1-yl)-1H-1,3-benzodiazol-2-yl]-1,3-dimethyl-1,2-dihydropyridin-2-one

HRID 930519Notes

Reaction equation

[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH:12]=[CH:11][C:10]=1[NH:22][C:23]([C:25]1[CH:30]=[C:29]([CH3:31])[C:28](=[O:32])[N:27]([CH3:33])[CH:26]=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C>[CH2:1]([N:8]1[C:9]2[CH:14]=[C:13]([N:15]3[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]3)[CH:12]=[CH:11][C:10]=2[N:22]=[C:23]1[C:25]1[CH:30]=[C:29]([CH3:31])[C:28](=[O:32])[N:27]([CH3:33])[CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1,5-Dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid [2-benzylamino-4-(4-methyl-piperazin-1-yl)-phenyl]-amide I-1′ (523.000 mg; 1.174 mmol) is dissolved in acetic acid and stirred at 80° C. overnight. The reaction mixture is concentrated under reduced pressure and the residue is purified on silica chromatography Combiflash (Column: Redisep Rf, 40 g; gradient: DCM/MeOH=100%/0% to 95%/5% over 30 column volumes, then to 90%/10% over 15 column volumes; flow rate=40 ml/min; detection wavelength: 254 nm). Product containing fractions are combined and concentrated under reduce pressure.

Workup

concentrationThe reaction mixture is concentrated under reduced pressure
customthe residue is purified on silica chromatography Combiflash (Column
additionProduct containing fractions
concentrationconcentrated

Sources & evidence

ORD record: ord-fe78a7f007604d288c7211e26e0b248d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296748B2

Reaction notes

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