Triethylamine → Propanamide, 3-chloro-N-1H-indazol-5-yl-

HRID 1269719Notes

Reaction equation

HRID 1269719 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][C:21](Cl)=[O:22]>O1CCCC1>[Cl:18][CH2:19][CH2:20][C:21]([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:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 693643-Chloropropionyl chlorideHCID 880121H-Indazol-5-amine

Product 1

HCID 17164503Propanamide, 3-chloro-N-1H-indazol-5-yl-Yield 44.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (1.6 ml, 30.0 mmol) was added to a solution of 5-aminoindazole (2.0 g, 15.0 mmol) in tetrahydrofuran (50 ml) at room temperature, followed by adding thereto 3-chloropropionyl chloride (1.43 ml, 15.0 mmol) at 0° C., and the resulting mixture was stirred at room temperature for 30 minutes. Then, the reaction solution was distilled under reduced pressure to remove the solvent, and the resulting residue was suspended in ethanol and stirred. Thereafter, the solid was collected by filtration and dried under reduced pressure to obtain 3-chloro-N-(1H-indazol-5-yl)propanamide (1.49 g, 44%).

Workup

  1. additionby adding
  2. distillationThen, the reaction solution was distilled under reduced pressure
  3. customto remove the solvent
  4. filtrationThereafter, the solid was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-0137b3d7e2de4412b4da6a0089bd24c3
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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