Sodium Iodide → HCID 57717624, compound

HRID 1984493Notes

Reaction equation

HRID 1984493 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[N:7]([CH2:20][CH2:21][O:22][CH3:23])[N:8]=[C:9]2[C:18]=1[C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:11]=[C:10]2[NH2:19].[CH3:24][S:25]([NH2:28])(=[O:27])=[O:26].[H-].[Na+].[I-].[Na+]>>[NH2:19][C:10]1[C:9]2=[N:8][N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:28][S:25]([CH3:24])(=[O:27])=[O:26])=[C:18]2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 57717528HCID 57717528, compound

Product 1

HCID 57717624HCID 57717624, compound

Procedure

The method described in Example 1254 was used to treat 1-(4-chlorobutyl)-2-(2-methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-4-amine (1.1 g, 3.3 mmol) with methanesulfonamide pretreated with sodium hydride in the presence of sodium iodide. The crude was purified by chromatography using a HORIZON HPFC system (40+M cartridge, eluting with 0-30% CMA in chloroform) followed by recrystallization from acetonitrile to provide 600 mg of N-{4-[4-amino-2-(2-methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]butyl}methanesulfonamide as white crystals, mp 159-161° C.

Workup

  1. customThe crude was purified by chromatography
  2. washa HORIZON HPFC system (40+M cartridge, eluting with 0-30% CMA in chloroform)
  3. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-2a7e969dbe4c44068db7cedb22521524
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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