Triethylamine → HCID 67214572, compound

HRID 2420764Notes

Reaction equation

HRID 2420764 reaction equation
C(OP(C#[N:10])(=O)OCC)C.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]3[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=3)[C:27]([OH:29])=O)[N:18]=2)[CH:12]=1.[CH3:33][N:34]1[CH2:39][CH2:38][N:37]([CH2:40]C2C=CC(N)=CC=2)[CH2:36][CH2:35]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O.O>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]3[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=3)[C:27]([NH:10][CH2:40][N:37]3[CH2:36][CH2:35][N:34]([CH3:33])[CH2:39][CH2:38]3)=[O:29])[N:18]=2)[CH:12]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 516892Sodium BicarbonateHCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 10039959HCID 10039959, compound

Product 1

HCID 67214572HCID 67214572, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Diethylcyanophosphonate (Aldrich, Buchs, Switzerland; 0.50 mL, 3.0 mmol) is added to a stirred mixture of 3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-benzoic acid (438 mg, 1.5 mmol), 4-[(4-methyl-1-piperazinyl)methyl]benzeneamine (308 mg, 1.5 mmol) and triethylamine (840 μL, 3.0 mmol) in 10 mL N,N-dimethylformamide at 10° C. After stirring for 12 hours at 60° C., the mixture is treated with an aqueous solution of sodium hydrogen carbonate and extracted three times with ethyl acetate. The combined extracts are washed with water, and the solvent is evaporated off under reduced pressure to give a residue. The residue is resuspended in water and filtered to afford the crude product which is recrystallised from tetrahydrofuran-ethyl acetate to give N-[3-[[4-(3-Pyridinyl)-2-pyrimidinyl]amino]-N-[(4-methyl-1-piperazinyl)-methyl]benzamide as a crystalline solid, m.p. 220-224° C.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined extracts are washed with water
  3. customthe solvent is evaporated off under reduced pressure
  4. customto give a residue
  5. filtrationfiltered
  6. customto afford the crude product which
  7. customis recrystallised from tetrahydrofuran-ethyl acetate

Sources & evidence

ORD record
ord-28feace226d549f2a325a5ae69680372
Source dataset
uspto-grants-2011_06
Patent number
US07956053B2

Reaction notes

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