1-Hydroxybenzotriazole → HCID 18447367, compound

HRID 1269890Notes

Reaction equation

HRID 1269890 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13]([OH:15])=O)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH2:20]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.[OH-].[Na+]>[CH2:20]([N:27]1[CH2:32][CH2:31][N:30]([C:13]([C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[NH:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)=[O:15])[CH2:29][CH2:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 759941-BenzylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14790454HCID 14790454, compound

Product 1

HCID 18447367HCID 18447367, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-(1H-indazol-5-ylamino)benzoic acid (102 mg, 0.402 mmol) in N,N-dimethylformamide (0.5 ml) were added 1-benzylpiperazine (210 μl, 1.21 mmol), 1-hydroxybenzotriazole (74 mg, 0.484 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (94 mg, 0.490 mmol) in that order, and the resulting mixture was stirred at room temperature for 21 hours. The mixture was dissolved in a 2N-aqueous sodium hydroxide solution (10 ml) and then extracted twice with ethyl acetate/toluene/tetrahydrofuran (2/2/1, 10 ml). The extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby a crude product was obtained. The crude product was purified by a silica gel column chromatography (eluent: chloroform/methanol=100/3) to obtain N-{2-[(4-benzylpiperazin-1-yl)carbonyl]phenyl}-1H-indazol-5-amine (162 mg, 100%).

Workup

  1. extractionextracted twice with ethyl acetate/toluene/tetrahydrofuran (2/2/1, 10 ml)
  2. washThe extract solution was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent, whereby a crude product
  6. customwas obtained
  7. customThe crude product was purified by a silica gel column chromatography (eluent: chloroform/methanol=100/3)

Sources & evidence

ORD record
ord-9f58eccd255349d99d93c87801b29256
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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