2-Dimethylaminopyridine → HCID 131726449, compound

HRID 1352136Notes

Reaction equation

HRID 1352136 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([NH2:13])[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)=[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:57](=O)([O-])[OH:58].[Na+]>CN(C)C=O>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:57]([CH2:23][C:19]2[CH:18]=[C:17]3[C:22](=[CH:21][CH:20]=2)[NH:14][N:15]=[CH:16]3)=[O:58])[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 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27566131-Benzyl-3-aminopyrrolidineHCID 42484541H-Indazole-5-carboxylic acid2×

Product 1

HCID 131726449HCID 131726449, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Benzyl-3-aminopyrrolidine (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 (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 (21 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-47871e6f541f41469a4e3ef15ab4ce92
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

Loading…