Water → HCID 178505016, compound

HRID 1822239Notes

Reaction equation

HRID 1822239 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[C:14]3[C:15](=[O:29])[N:16]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:17]4[N:18]=[CH:19][CH:20]=[CH:21][C:22]=4[C:13]=3[NH:12][N:11]=2)=[CH:4][CH:3]=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32].O>N1C=CC=CC=1>[CH3:30][S:31]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[C:14]3[C:15](=[O:29])[N:16]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:17]4[N:18]=[CH:19][CH:20]=[CH:21][C:22]=4[C:13]=3[NH:12][N:11]=2)=[CH:4][CH:3]=1)(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 178507550HCID 178507550, compound

Product 1

HCID 178505016HCID 178505016, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-[2-(4-aminophenyl)ethyl]-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (38 mg, 0.10 mmol, prepared in Example 13) in pyridine (2 ml) was added methanesulfonyl chloride (18.5 mg, 0.16 mmol, 1.6 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 to afford 3-[2-(4-methanesulfonylaminophenyl)ethyl]-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (43 mg, 86%).

Workup

  1. filtrationfiltered
  2. customto give
  3. customprecipitates which
  4. customwere dried

Sources & evidence

ORD record
ord-8fb19b68f3af4b62ac1717c95bbaa83c
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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