1-Methylpiperazine → 5-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1693536Notes

Reaction equation

HRID 1693536 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[Cl:34])=[CH:4][CH:3]=1.[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>S(Cl)(Cl)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:19]=[CH:20][C:21]([C:22]([N:39]5[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]5)=[O:24])=[CH:25][CH:26]=4)[C:11]=3[N:10]=[C:9]2[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[Cl:34])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 578980584-[5-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzoic acid

Product 1

HCID 578979085-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

4-[5-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzoic acid (54.1 mg, 0.106 mmol) is dissolved in 1 mL of thionyl chloride and stirred for 1 h at reflux. The thionyl chloride is then removed under a stream of dry nitrogen and the resulting solid is dissolved in 2 mL of dry dichloromethane. N-methylpiperazine (500 mg, 5.00 mmol) is then added to the solution and the reaction mixture is stirred for 2 h. After the volatiles are evaporated, the resulting residue is dissolved in 1 M NaOH and extracted with ethyl acetate. The crude product is purified by column chromatography. 1H NMR (CDCl3, 400 MHz) δ 8.36(s, 1H), 8.28 (d, 2H), 7.57 (d, 2H), 7.36-7.29 (m, 3H), 7.23-7.16 (m, 2H), 7.03 (m, 1H), 3.97 (m, 3H), 3.48 (m, 2H), 2.83 (m, 6H). HPLC-MS calculated for C29H23Cl3N6O2 (M+H+) 593.1. Found: 593.1.

Workup

  1. temperatureat reflux
  2. customThe thionyl chloride is then removed under a stream of dry nitrogen
  3. dissolutionthe resulting solid is dissolved in 2 mL of dry dichloromethane
  4. stirringthe reaction mixture is stirred for 2 h
  5. customAfter the volatiles are evaporated
  6. dissolutionthe resulting residue is dissolved in 1 M NaOH
  7. extractionextracted with ethyl acetate
  8. customThe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-e0975dd7278640aca05c25edffb1b071
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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