Triethylamine → 4-Chloro-N-1H-indazol-5-ylbutanamide

HRID 1269726Notes

Reaction equation

HRID 1269726 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[CH:12]2.[Cl:18][CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23].[OH-].[Na+]>O1CCCC1>[Cl:18][CH2:19][CH2:20][CH2:21][C:22]([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[CH:12]2)=[O:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 783704-Chlorobutyryl chlorideHCID 880121H-Indazol-5-amine

Product 1

HCID 171645134-Chloro-N-1H-indazol-5-ylbutanamideYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triethylamine (2.1 ml, 15 mmol) was added to a suspension of 5-aminoindazole (1.00 g, 7.51 mmol) in tetrahydrofuran (10 ml) at room temperature, followed by adding thereto a solution of 4-chlorobutyryl chloride (1.16 g, 8.26 mmol) in tetrahydrofuran (5 ml) at 0° C., and the resulting mixture was stirred at 0° C. for 1 hour. Then, a 1N-aqueous sodium hydroxide solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was suspended in ethanol and stirred, followed by filtration. The solid collected by the filtration was dried under reduced pressure to obtain 4-chloro-N-(1H-indazol-5-yl)butanamide (572 mg, 32%).

Workup

  1. additionby adding
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. filtrationfollowed by filtration
  7. filtrationThe solid collected by the filtration
  8. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-6154b572fc744a7191e0743240d7c548
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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