Acetyl chloride → HCID 22933727, compound

HRID 1269716Notes

Reaction equation

HRID 1269716 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[CH:18]3)[CH2:10][CH2:9]1.[C:24](Cl)(=[O:26])[CH3:25].[OH-].[Na+]>O1CCCC1>[C:24]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[CH:18]3)[CH2:12][CH2:13]1)(=[O:26])[CH3:25]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 9899273HCID 9899273, compound2×

Product 1

HCID 22933727HCID 22933727, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triethylamine (0.39 ml, 2.80 mmol) was added to a solution of the N-(4-piperidinyl)-1H-indazol-5-amine (0.301 g, 1.39 mmol) obtained in Example 15, (a) in tetrahydrofuran (5 ml) at room temperature, followed by adding thereto a solution of acetyl chloride (0.12 g, 1.53 mmol) in tetrahydrofuran (2 ml) at 0° C., and the resulting mixture was stirred at room temperature for 1 hour. Then, the reaction solution was poured into a 1N-aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was suspended in acetone and stirred. Thereafter, the solid was collected by filtration and dried under reduced pressure to obtain N-(1-acetyl-4-piperidinyl)-1H-indazol-5-amine (0.216 g, 60%).

Workup

  1. additionby adding
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. filtrationThereafter, the solid was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-ea829970af1d4ce7837fc001162a821f
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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