Ethanesulfonylchloride, 2-chloro- → HCID 135599964, compound

HRID 1175817Notes

Reaction equation

HRID 1175817 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][CH2:25][S:26](Cl)(=[O:28])=[O:27].C(N(C(C)C)CC)(C)C.[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>O.CN(C)C=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][S:26]([CH2:25][CH2:24][N:43]4[CH2:44][CH2:45][N:40]([CH3:39])[CH2:41][CH2:42]4)(=[O:28])=[O:27])=[CH:10][C:9]=3[NH:8][C:7](=[O:16])[C:6]=12

Participants

8

Reactant 4

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 135599894HCID 135599894, compound

Product 1

HCID 135599964HCID 135599964, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,7-diamino-2-phenyl-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one (150 mg), 2-chloroethanesulfonyl chloride (61.8 μl), diisopropylethylamine (108 μl) and tetrahydrofuran (5 ml) was stirred at room temperature for 30 minutes, 1-methylpiperazine (571 μl) and N,N-dimethylformamide (1 ml) were added thereto, and stirred at room temperature for one night. 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. The residue was purified with aminopropylated silica gel column chromatography to obtain the target compound (25 mg).

Workup

  1. stirringstirred at room temperature for one night
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified with aminopropylated silica gel column chromatography

Sources & evidence

ORD record
ord-e78c28a9fe954fa888633e9777655ba8
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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