2-Dimethylaminopyridine → HCID 131726449, compound

HRID 1352137Notes

Reaction equation

HRID 1352137 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4]C1.[NH:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24](O)=O)=[CH:21][CH:22]=2)[CH:17]=[N:16]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN(C1C=CC=CN=1)C.[C:58](=O)([O-])[OH:59].[Na+]>CN(C)C=O>[CH2:8]([N:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:58]([CH2:24][C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[NH:15][N:16]=[CH:17]3)=[O:59])[CH2:4]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 6

HCID 218852-DimethylaminopyridineHCID 757711-HydroxybenzotriazoleHCID 4158521-Benzyl-4-piperidylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 42484541H-Indazole-5-carboxylic acid2×

Product 1

HCID 131726449HCID 131726449, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-1-benzylpiperidine (280 mg) and 1H-5-indazolecarboxylic acid (intermediate 2) (243 mg) were dissolved in dimethylformamide (3 ml), and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (383 mg), 1-hydroxybenzotriazole (306 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 (42 mg).

Workup

  1. addition(5 mg) were added to the solution
  2. extractionthe mixture was extracted with chloroform-propanol (3/1)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by HPLC [chloroform/methanol]

Sources & evidence

ORD record
ord-80a650ddf8db437196d1b52d11e1bd37
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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