Chloroacetyl chloride → HCID 135600033, compound

HRID 1175816Notes

Reaction equation

HRID 1175816 reaction equation
[NH2:1][C:2]1[N:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([NH2:15])=[CH:10][C:9]=3[NH:8][C:7](=[O:16])[C:6]=12.Cl[CH2:24][C:25](Cl)=[O:26].C(N(CC)CC)C.[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>O.O1CCCC1>[NH2:1][C:2]1[N:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([NH:15][C:25](=[O:26])[CH2:24][N:39]4[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]4)=[CH:10][C:9]=3[NH:8][C:7](=[O:16])[C:6]=12

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 135599894HCID 135599894, compound

Product 1

HCID 135600033HCID 135600033, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,7-diamino-2-phenyl-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one (100 mg), chloroacetyl chloride (28.6 μl), triethylamine (71.7 μl ) and tetrahydrofuran (6 ml) was stirred at room temperature for 30 minutes, and 1-methylpiperazine (76.1 μl) was added thereto. The reaction mixture was stirred at room temperature for additional 30 minutes and with heating under reflux for 6 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue. The precipitated solid was collected by filtration, and washed with ethyl acetate to obtain the target compound (64 mg).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for additional 30 minutes
  2. temperaturewith heating
  3. temperatureunder reflux for 6 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionEthyl acetate was added to the residue
  9. filtrationThe precipitated solid was collected by filtration
  10. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-0bfd633227f440f9972bc86a8adf0c34
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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