2-Dimethylaminopyridine → HCID 17838263, compound

HRID 1352143Notes

Reaction equation

HRID 1352143 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[NH:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([CH:21]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:22](O)=[O:23])[CH2:16]3)=[CH:11][CH:12]=2)[CH:7]=[N:6]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>[CH:1]1([NH:4][C:22](=[O:23])[CH:21]([N:17]2[CH2:18][CH2:19][CH2:20][CH:15]([NH:14][C:10]3[CH:9]=[C:8]4[C:13](=[CH:12][CH:11]=3)[NH:5][N:6]=[CH:7]4)[CH2:16]2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 6

HCID 218852-DimethylaminopyridineHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 17838237HCID 17838237, compound

Product 1

HCID 17838263HCID 17838263, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyclopropylamine (30 mg) and the compound prepared in Example 222 (88 mg) were dissolved in dimethylformamide (1 ml), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydro-chloride (86 mg), 1-hydroxybenzotriazole (77 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 (1 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]t to give 64 mg of the title compound as a single diastereomers.

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]t

Sources & evidence

ORD record
ord-eda0fe86118a4e0e81cca57efdf01e2e
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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