Water → HCID 67402462, compound

HRID 1186309Notes

Reaction equation

HRID 1186309 reaction equation
[F:1][C:2]([F:23])([F:22])[CH:3]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[O:4][C:5]1[N:10]=[C:9]2[CH:11]=[N:12][CH:13]=[CH:14][C:8]2=[N:7][C:6]=1[NH2:15].[CH2:24]([S:27](Cl)(=[O:29])=[O:28])[CH2:25][CH3:26].[H-].[Na+].O>C1COCC1.C(OCC)(=O)C>[F:23][C:2]([F:1])([F:22])[CH:3]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[O:4][C:5]1[N:10]=[C:9]2[CH:11]=[N:12][CH:13]=[CH:14][C:8]2=[N:7][C:6]=1[NH:15][S:27]([CH2:24][CH2:25][CH3:26])(=[O:29])=[O:28]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 662791-Propanesulfonyl chlorideHCID 67401626HCID 67401626, compound

Product 1

HCID 67402462HCID 67402462, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

3-[2,2,2-Trifluoro-1-(pyridin-3-yl)ethoxy]-pyrido[3,4-b]pyrazin-2-amine (100 mg, 0.310 mmol) obtained in Step 2 was dissolved in THF (2.50 mL). To this, propane-1-sulfonyl chloride (0.094 mL, 0.840 mmol) and 60% sodium hydride (in oil) (23.0 mg, 0.560 mmol) were added, and the mixture was stirred with heat at 80° C. for 4 hours. The reaction was stopped by addition of water to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=1/0 to 16/1) was performed to give Compound 361 (40.0 mg, yield: 30%).

Workup

  1. washby washing with brine
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. customThe solvent was evaporated off under reduced pressure, and purification by silica gel column chromatography (chloroform/methanol=1/0 to 16/1)

Sources & evidence

ORD record
ord-e0e4b0ce6b984a9188006ddd8df23951
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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