Triethylamine → HCID 178503435, compound

HRID 1809694Notes

Reaction equation

HRID 1809694 reaction equation
Cl[C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)[C:5]2=[CH:4][N:3]=1.[N:19]1([CH2:25][CH2:26][NH2:27])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(CC)CC)C>CC(O)C>[CH3:18][S:17][C:13]1[N:12]=[C:11]([C:10]2[C:5]3[C:6](=[N:7][C:2]([NH:27][CH2:26][CH2:25][N:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)=[N:3][CH:4]=3)[NH:8][N:9]=2)[CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 33944N-(2-Aminoethyl)piperidineHCID 178503430HCID 178503430, compound

Product 1

HCID 178503435HCID 178503435, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 6-chloro-3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidine (from Example 7 supra) (450 mg, 1.61 mmol) in 2-propanol (40 mL) was added 2-(piperidin-1-yl)ethanamine (227 mg, 1.77 mmol) followed by triethylamine (160 mg, 1.58 mmol). The reaction mixture was stirred at reflux for 15 hours and the solvent was then removed under reduced pressure. The residue was extracted with dichloromethane (3×30 mL), washed with water (5 mL), dried over anhydrous sodium sulfate, filtered and concentrated to afford [3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-piperidin-1-yl-ethyl)-amine. (Yield 411 mg, crude).

Workup

  1. temperatureat reflux for 15 hours
  2. customthe solvent was then removed under reduced pressure
  3. extractionThe residue was extracted with dichloromethane (3×30 mL)
  4. washwashed with water (5 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2a410327da10461c91507e4020e16958
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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