Triethylamine → 1,5-Dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid [2-benzylamino-4-(4-methyl-piperazin-1-yl)-phenyl]-amide

HRID 930518Notes

Reaction equation

HRID 930518 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([CH3:9])=[CH:5][C:4]([C:10]([OH:12])=O)=[CH:3]1.[CH2:13]([NH:20][C:21]1[C:22]([NH2:34])=[CH:23][CH:24]=[C:25]([N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)[CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C1COCC1>[CH2:13]([NH:20][C:21]1[CH:26]=[C:25]([N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)[CH:24]=[CH:23][C:22]=1[NH:34][C:10]([C:4]1[CH:5]=[C:6]([CH3:9])[C:7](=[O:8])[N:2]([CH3:1])[CH:3]=1)=[O:12])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 218859251,5-Dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acidHCID 901610111-N-benzyl-5-(4-methylpiperazin-1-yl)benzene-1,2-diamine

Product 1

HCID 1178940361,5-Dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid [2-benzylamino-4-(4-methyl-piperazin-1-yl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1,5-dimethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid D1 (210.000 mg; 1.256 mmol), N2-Benzyl-4-(4-methyl-piperazin-1-yl)-benzene-1,2-diamine E-1.1 (363.000 mg; 1163.422 μmol) and triethylamine (0.435 ml; 3.141 mmol) in THF (3.000 ml) is added N-propylphosphonic acid anhydride, cyclic trimer (0.880 ml; 1.508 mmol). The mixture is stirred for 5 h at RT. The reaction is quenched with 1M NaOH, diluted with 50 ml water and extracted twice with ethyl acetate (50 ml). The combined organic layer is dried over Na2SO4 and concentrated in vacuum. The residue is used in the next step without further purification

Workup

  1. customThe reaction is quenched with 1M NaOH
  2. additiondiluted with 50 ml water
  3. extractionextracted twice with ethyl acetate (50 ml)
  4. dry with materialThe combined organic layer is dried over Na2SO4
  5. concentrationconcentrated in vacuum
  6. customThe residue is used in the next step without further purification

Sources & evidence

ORD record
ord-91cd0b59566b43928beb5b131df8c553
Source dataset
uspto-grants-2016_03
Patent number
US09296748B2

Reaction notes

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