Methanesulfonyl chloride → HCID 57717560, compound

HRID 1360527Notes

Reaction equation

HRID 1360527 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]([CH3:28])([CH3:27])[CH2:8][C:9]1[N:10]([CH2:23][CH2:24][O:25][CH3:26])[N:11]=[C:12]2[C:21]=1[C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:14]=[C:13]2[NH2:22]>C(OCC)(=O)C>[NH2:22][C:13]1[C:12]2=[N:11][N:10]([CH2:23][CH2:24][O:25][CH3:26])[C:9]([CH2:8][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])([CH3:28])[CH3:27])=[C:21]2[C:20]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:14]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 57717558HCID 57717558, compound

Product 1

HCID 57717560HCID 57717560, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Using the method of Example 66, methanesulfonyl chloride (399 mg, 3.48 mmol) was reacted with 1-(2-amino-2-methylpropyl)-2-(2-methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-4-amine (1.09 g, 3.48 mmol, prepared as described in Example 590). The crude product was purified by IFC (40M cartridge eluting with a gradient of 15 to 35% CMA in chloroform) to provide a white foam. The foam was refluxed with 35% ethyl acetate in hexanes (50 mL), ethyl acetate was added until a free flowing white solid appeared, and then the mixture was cooled on ice. The solid was isolated by filtration and dried to provide 809 mg of N-{2-[4-amino-2-(methoxyethyl)-2H-pyrazolo[3,4-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide as a white solid, mp 211-213° C. MS (ESI) m/z 392 (M+H)+; Anal. Calcd for C18H25N5O3S: C, 55.22; H, 6.44; N, 17.89. Found: C, 55.05; H, 6.38; N, 17.98.

Workup

  1. customThe crude product was purified by IFC (40M cartridge
  2. washeluting with a gradient of 15 to 35% CMA in chloroform)
  3. customto provide a white foam
  4. additionwas added until
  5. temperaturethe mixture was cooled on ice
  6. customThe solid was isolated by filtration
  7. customdried

Sources & evidence

ORD record
ord-6f054be4cc524dc7b9c44ceb091028d6
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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