2-Dimethylaminopyridine → HCID 17838189, compound

HRID 1352135Notes

Reaction equation

HRID 1352135 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:14]1[C:22]2[C:17](=[CH:18][C:19]([C:23](O)=[O:24])=[CH:20][CH:21]=2)[CH:16]=[N:15]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN(C1C=CC=CN=1)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:23]([C:19]2[CH:18]=[C:17]3[C:22](=[CH:21][CH:20]=2)[NH:14][N:15]=[CH:16]3)=[O:24])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 218852-DimethylaminopyridineHCID 757711-HydroxybenzotriazoleHCID 759941-BenzylpiperazineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 42484541H-Indazole-5-carboxylic acid2×

Product 1

HCID 17838189HCID 17838189, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Benzylpiperazine (256 mg) and 1H-5-indazolecarboxylic acid (intermediate 2) (243 mg) were dissolved in dimethylformamide (3 ml), and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (263 mg), 1-hydroxybenzotriazole (225 mg), and dimethylaminopyridine (5 mg) were added to the solution. The reaction mixture was stirred at room temperature for 18 hr. A saturated aqueous sodium hydrogencarbonate solution (2 ml) was then added thereto, and the mixture was extracted with chloroform-propanol (3/1). The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by HPLC [chloroform/methanol] to give the title compound (30 mg).

Workup

  1. extractionthe mixture was extracted with chloroform-propanol (3/1)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed by distillation under the reduced pressure
  4. customThe residue was purified by HPLC [chloroform/methanol]

Sources & evidence

ORD record
ord-865b13f3e1bb4d5389c41801404fe6d3
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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