Water → HCID 57717610, compound

HRID 2283888Notes

Reaction equation

HRID 2283888 reaction equation
[NH2:1][C:2]([CH3:21])([CH3:20])[CH2:3][C:4]1[N:5]([CH2:18][CH3:19])[N:6]=[C:7]2[C:16]=1[C:15]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:9]=[C:8]2[NH2:17].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].O>ClCCl>[NH2:17][C:8]1[C:7]2=[N:6][N:5]([CH2:18][CH3:19])[C:4]([CH2:3][C:2]([NH:1][S:30]([CH3:29])(=[O:32])=[O:31])([CH3:20])[CH3:21])=[C:16]2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57717510HCID 57717510, compound

Product 1

HCID 57717610HCID 57717610, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, a solution of 1-(2-amino-2-methylpropyl)-2-ethyl-2H-pyrazolo[3,4-c]quinolin-4-amine (609 mg, 2.15 mmol) in dichloromethane (60 mL) was cooled to 0° C. Triethylamine (326 mg, 3.22 mmol) and methanesulfonyl chloride (246 mg, 2.15 mmol) were sequentially added. The reaction was stirred at 0° C. for five hours and then allowed to warm to room temperature slowly and stirred overnight. Water was added, and the aqueous layer was separated and extracted four times with chloroform. The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by TFC (silica cartridge) followed by recrystallization from acetonitrile. The crystals were dried overnight on the vacuum filter funnel to provide 363 mg of N-[2-(4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-1-yl)-1,1-dimethylethyl]methanesulfonamide as a white solid, mp 229-230° C.

Workup

  1. temperatureto warm to room temperature slowly
  2. stirringstirred overnight
  3. customthe aqueous layer was separated
  4. extractionextracted four times with chloroform
  5. dry with materialThe combined organic fractions were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by TFC (silica cartridge)
  9. customfollowed by recrystallization from acetonitrile
  10. customThe crystals were dried overnight on the vacuum
  11. filtrationfilter funnel

Sources & evidence

ORD record
ord-4c304b37b10c496192042a23033d8e2e
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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