Triethylamine → HCID 9901752, compound

HRID 1593993Notes

Reaction equation

HRID 1593993 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O)#[N:2].C(Cl)(=O)C(Cl)=O.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[N:21]=1.C(N(CC)CC)C>C(Cl)Cl.N1C=CC=CC=1>[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([N:29]1[CH2:30][CH2:31][N:26]([C:22]2[N:21]=[C:20]([O:19][CH3:18])[CH:25]=[CH:24][N:23]=2)[CH2:27][CH2:28]1)=[O:7])#[N:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1380612-Cyanobenzoic acidHCID 114809874-Methoxy-2-(piperazin-1-yl)pyrimidine

Product 1

HCID 9901752HCID 9901752, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 2.0 g (14 mmol) of 2-cyanobenzoic acid in 100 mL of CH2Cl2 are added 1.5 mL (17.5 mmol) of oxalyl chloride and a catalytic amount of pyridine. The suspension is left stirred at room temperature for 3 hours. The solvent is evaporated at reduced pressure, giving a crude which is suspended in 100 mL of CH2Cl2 and which is slowly added on a solution of 2.45 g (12.6 mmol) of 4-methoxy-2-(1-piperazinyl)pyrimidine and 4 mL (28 mmol) of triethylamine in 50 mL of CH2Cl2 cooled to 0° C. in an ice bath. The solution is kept at 0° C. for one hour and is allowed to reach room temperature. The reaction mixture is washed with H2O, dried with Na2SO4 and the solvent eliminated at reduced pressure. The resulting crude is purified by chromatography on silica gel, using ethyl acetate as eluent, providing 2.06 g (6.4 mmol) of 2-[4-(2-cyanobenzoyl)-1-piperazinyl]-4-methoxipyrimidine with m.p.=166-168° C.

Workup

  1. waitThe suspension is left
  2. customThe solvent is evaporated at reduced pressure
  3. customgiving a crude which
  4. temperaturecooled to 0° C. in an ice bath
  5. waitThe solution is kept at 0° C. for one hour
  6. customto reach room temperature
  7. washThe reaction mixture is washed with H2O
  8. dry with materialdried with Na2SO4
  9. customThe resulting crude is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-82b40358aa2f4078843d46f94c931e25
Source dataset
uspto-grants-2007_11
Patent number
US07300937B2

Reaction notes

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