Triethylamine → HCID 68527387, compound

HRID 1932488Notes

Reaction equation

HRID 1932488 reaction equation
[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=1)[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[CH2:21]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>CN(C=O)C.O>[CH2:21]([N:28]1[CH2:33][CH2:32][N:31]([C:7]([C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[C:12]3[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][N:13]=3)=[CH:11][CH:10]=2)=[O:9])[CH2:30][CH2:29]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 76257Diethyl cyanophosphonateHCID 68525775HCID 68525775, compound

Product 1

HCID 68527387HCID 68527387, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[methyl-(5-nitropyridin-2-yl)amino]benzoic acid (0.800 g, 2.93 mmol) and 1-benzylpiperazine (0.542 g, 3.08 mmol) in DMF (15 mL) were added triethylamine (1.02 mL, 7.32 mmol) and diethyl cyanophosphonate (0.593 mL, 3.52 mmol), and the resulting solution was stirred for 3 hours. To the resulting reaction solution was added water 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 (ethyl acetate), to thereby yield 1.25 g of the title compound.

Workup

  1. customTo the resulting reaction solution
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-27712a7f7d48471eb3c2c44c6c6e5b48
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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