1,5-Dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (4-benzylamino-6-morpholin-4-yl-pyridin-3-yl)-amide → 5-(1-Benzyl-6-morpholin-4-yl-1H-imidazo[4,5-c]pyridin-2-yl)-1,3-dimethyl-1H-pyridin-2-one

HRID 930527Notes

Reaction equation

HRID 930527 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:12]=[CH:11][C:10]=1[NH:21][C:22]([C:24]1[CH:29]=[C:28]([CH3:30])[C:27](=[O:31])[N:26]([CH3:32])[CH:25]=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[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[N:12]=[CH:11][C:10]=2[N:21]=[C:22]1[C:24]1[CH:29]=[C:28]([CH3:30])[C:27](=[O:31])[N:26]([CH3:32])[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 1178940391,5-Dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (4-benzylamino-6-morpholin-4-yl-pyridin-3-yl)-amide

Product 1

HCID 1178919575-(1-Benzyl-6-morpholin-4-yl-1H-imidazo[4,5-c]pyridin-2-yl)-1,3-dimethyl-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

1,5-Dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (4-benzylamino-6-morpholin-4-yl-pyridin-3-yl)-amide II-3′ (73.000 mg; 0.168 mmol) is dissolved in acetic acid (2.1 g) and stirred at 150° C. for 10 h in the microwave. The reaction mixture is concentrated under reduced pressure. The residue is purified on silica chromatography Combiflash (Column: Redisep Rf, 12 g; gradient: DCM/MeOH=100%/0% to 90%/10%; flow rate=30 ml/min; 28 column volumes; detection wavelength: 254 nm). The product containing fractions are combined and concentrated under reduce pressure. The residue is then dissolved in acetonitrile:water 1:1 and freeze dried

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customThe residue is purified on silica chromatography Combiflash (Column: Redisep Rf, 12 g; gradient: DCM/MeOH=100%/0% to 90%/10%; flow rate=30 ml/min; 28 column volumes; detection wavelength: 254 nm)
  3. additionThe product containing fractions
  4. concentrationconcentrated
  5. dissolutionThe residue is then dissolved in acetonitrile:water 1:1 and freeze
  6. customdried

Sources & evidence

ORD record
ord-3c2901126a744e128952891a714b1687
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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