Cyclopropylamine → HCID 10378644, compound

HRID 606026Notes

Reaction equation

HRID 606026 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:3]=12.[CH:18]1([NH2:21])[CH2:20][CH2:19]1>C(#N)C>[CH2:11]([O:10][C:8]([C:7]1[C:2]([NH:21][CH:18]2[CH2:20][CH2:19]2)=[C:3]2[CH:15]=[N:14][N:13]([CH2:16][CH3:17])[C:4]2=[N:5][CH:6]=1)=[O:9])[CH3:12]

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 10491120ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 10378644HCID 10378644, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (950 mg, 0.0037 mole) in acetonitrile, cyclopropyl amine (0.525 ml, 0.0074 mole) was added. After stirring for about 2 hours at 110° C., acetonitrile was removed under reduced pressure. Water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give light yellow solid compound. Yield: 1 g. m/z: (M++1) 275.0.

Workup

  1. additionwas added
  2. customacetonitrile was removed under reduced pressure
  3. additionWater was added
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give light yellow solid compound

Sources & evidence

ORD record
ord-d03241eee38844488cdc0af8bd6dd8e0
Source dataset
uspto-grants-2011_03
Patent number
US07915286B2

Reaction notes

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