Triethylamine → HCID 22933578, compound

HRID 1269721Notes

Reaction equation

HRID 1269721 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[CH3:11][CH:12]([CH3:18])[CH2:13][CH2:14][C:15](O)=[O:16].Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.[OH-].[Na+]>CN(C)C=O>[NH:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][C:15](=[O:16])[CH2:14][CH2:13][CH:12]([CH3:18])[CH3:11])=[CH:10][CH:9]=2)[CH:5]=[N:6]1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 12587Isocaproic acidHCID 14798Sodium HydroxideHCID 880121H-Indazol-5-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 22933578HCID 22933578, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-aminoindazole (1.00 g, 7.51 mmol) in N,N-dimethylformamide (15 ml) were added 4-methylvaleric acid (960 mg, 8.26 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (1.72 g, 9.01 mmol), hydroxybenzotriazole (1.12 g, 8.26 mmol) and triethylamine (1.7 ml, 12.0 mmol), and the resulting mixture was stirred overnight at room temperature. Then, the reaction solution was cooled to 0° C. and a 1N-aqueous sodium hydroxide solution was added thereto, followed by extraction with chloroform. The organic layer was washed with water and then a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was dissolved in a mixture of diethyl ether and methanol, followed by adding thereto hexane. The solid precipitated was collected by filtration and dried under reduced pressure to obtain N-(1H-indazol-5-yl)-4-methylpentanamide (1.24 g, 71%).

Workup

  1. temperatureThen, the reaction solution was cooled to 0° C.
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. dissolutionthe resulting residue was dissolved in a mixture of diethyl ether and methanol
  7. additionby adding
  8. customThe solid precipitated
  9. filtrationwas collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-f7c2bd37db8d4314ac9996e4cc5da421
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

Loading…