Sodium methanethiolate → 1-(4-methylthiobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine

HRID 1984478Notes

Reaction equation

HRID 1984478 reaction equation
[CH3:1][S-:2].[Na+].Cl[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[N:10]([CH2:23][CH2:24][CH3:25])[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]>CN(C=O)C.ClCCl>[CH3:1][S:2][CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[N:10]([CH2:23][CH2:24][CH3:25])[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]

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 577175341-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine

Product 1

HCID 669588151-(4-methylthiobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amineYield 100.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Sodium thiomethoxide (0.3 g, 3.79 mmol) was added to a solution of 1-(4-chlorobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine (1.0 g, 3.16 mmol) in 15 mL of DMF and heated for 3 hours at 80° C. The reaction mixture was allowed to cool to ambient temperature, diluted with dichloromethane, and washed with water. The aqueous layer was extracted with several additional portions of dichloromethane and the combined organic layers were washed with water, washed with brine, dried over magnesium sulfate, and concentrated to afford 1.04 g of 1-(4-methylthiobutyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine as a yellow solid.

Workup

  1. temperatureto cool to ambient temperature
  2. washwashed with water
  3. extractionThe aqueous layer was extracted with several additional portions of dichloromethane
  4. washthe combined organic layers were washed with water
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bf4f7165375c421e86eb4e2814588f43
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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