Methanesulfonyl chloride → HCID 10228158, compound

HRID 2215015Notes

Reaction equation

HRID 2215015 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[N:9]=[C:8]2[C:3]=1[C:4](=[O:31])[CH:5]=[C:6]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[N:7]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C(Cl)Cl>[CH3:32][S:33]([N:15]1[CH2:16][CH2:17][N:12]([C:10]2[N:9]=[C:8]3[C:3]([C:4](=[O:31])[CH:5]=[C:6]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:7]3[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:2]([CH3:1])[CH:11]=2)[CH2:13][CH2:14]1)(=[O:35])=[O:34]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 10223346HCID 10223346, compound

Product 1

HCID 10228158HCID 10228158, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-methyl-1-phenyl-2-phenylamino-7-piperazin-1-yl-1H-[1,8]naphthyridin-4-one (22.6 mg, 0.055 mmol) and MsCl (0.083 mmol, 0.006 mL) in CH2Cl2 (0.8 mL) was stirred at room temperature overnight at which time the solvent was removed in vacuo. The resulting residue was purified by prep-TLC to give 7-(4-methanesulfonyl-piperazin-1-yl)-5-methyl-1-phenyl-2-phenylamino-1H-[1,8]naphthyridin-4-one (3.4 mg, 6%): LCMS RT: 2.36 min, MH+: 490.3.

Workup

  1. customwas removed in vacuo
  2. customThe resulting residue was purified by prep-TLC

Sources & evidence

ORD record
ord-8f0286e4e68f49f4a3c2ff82c6db4035
Source dataset
uspto-grants-2006_09
Patent number
US07109196B2

Reaction notes

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