Triethylamine → HCID 17838189, compound

HRID 1269731Notes

Reaction equation

HRID 1269731 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH2:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.S([O-])(O)(=O)=O.[K+]>CN(C)C=O>[CH2:13]([N:20]1[CH2:25][CH2:24][N:23]([C:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)=[O:12])[CH2:22][CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 759941-BenzylpiperazineHCID 516920Potassium bisulfateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 42484541H-Indazole-5-carboxylic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 17838189HCID 17838189, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-indazole-5-carboxylic acid (400 mg, 2.47 mmol) in N,N-dimethylformamide (8 ml) were added 1-benzylpiperazine (435 mg 2.47 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide monohydrochloride (565 mg, 2.96 mmol), hydroxybenzotriazole (367 mg, 2.72 mmol) and triethylamine (0.56 ml, 3.95 mmol), and the resulting mixture was stirred overnight at room temperature. Then, a 10% aqueous potassium hydrogensulfate solution was added to the reaction solution, followed by extraction with chloroform. A 1N-aqueous sodium hydroxide solution was added to the aqueous layer, followed by extraction with chloroform. The combined 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 purified by a silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain 5-[(4-benzyl-1-piperazinyl)carbonyl]-1H-indazole (624 mg, 79%).

Workup

  1. extractionfollowed by extraction with chloroform
  2. additionA 1N-aqueous sodium hydroxide solution was added to the aqueous layer
  3. extractionfollowed by extraction with chloroform
  4. washThe combined organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-5834850453894caa97a4739b40482b42
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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