Triethylamine → N-[4-(3-cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxyphenyl]-N-(methylsulfonyl)methanesulfonamide

HRID 915957Notes

Reaction equation

HRID 915957 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:24])[C:11]3[C:16]([CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[N:15][N:14]([CH3:23])[C:12]=3[N:13]=2)=[C:4]([O:25][CH3:26])[CH:3]=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>O1CCCC1>[CH:17]1([C:16]2[C:11]3[C:10](=[O:24])[NH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([N:1]([S:28]([CH3:27])(=[O:30])=[O:29])[S:28]([CH3:27])(=[O:30])=[O:29])=[CH:3][C:4]=4[O:25][CH3:26])=[N:13][C:12]=3[N:14]([CH3:23])[N:15]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 1359488876-(4-Amino-2-methoxyphenyl)-3-cyclohexyl-1-methyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 136005960N-[4-(3-cyclohexyl-1-methyl-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-3-methoxyphenyl]-N-(methylsulfonyl)methanesulfonamideYield 76.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 6 ml tetrahydrofuran solution of 114 mg (0.323 mmol) of the compound obtained in Example 44, 49 μl (0.63 mmol) of methanesulfonyl chloride and 90 μl (0.65 mmol) of triethylamine were added, and the mixture was stirred at room temperature for 1 hour. Then, 23 μl (0.3 mmol) of methanesulfonyl chloride was further added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. Then, an aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with water and a saturated aqueous solution of sodium chloride. After the washed layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=30/1) to obtain 123 mg (75%) of the captioned compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with water
  4. dry with materialAfter the washed layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-b0009f8c48d341db8e88cc6b45071178
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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