Water → HCID 178505014, compound

HRID 1822240Notes

Reaction equation

HRID 1822240 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][C:7]2[C:11]3[C:12](=[O:26])[N:13]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:14]4[N:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]=3[NH:9][N:8]=2)=[CH:4][CH:3]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31].O>N1C=CC=CC=1>[CH3:29][S:30]([NH:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][C:7]2[C:11]3[C:12](=[O:26])[N:13]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:14]4[N:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:10]=3[NH:9][N:8]=2)=[CH:4][CH:3]=1)(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 178507538HCID 178507538, compound

Product 1

HCID 178505014HCID 178505014, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-(4-aminobenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (107 mg, 0.29 mmol, prepared in Example 43) in pyridine (2 ml) was added methanesulfonyl chloride (47 mg, 0.41 mmol, 1.4 eq.), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was admixed with water, and filtered to give precipitates which were dried and purified by flash column chromatography to afford 3-(4-methanesulfonylaminobenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (84 mg, 65%).

Workup

  1. filtrationfiltered
  2. customto give
  3. customprecipitates which
  4. customwere dried
  5. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-14a95486e7cd4824a7d0620c4d8d8e43
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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