Diethylamine → HCID 17838152, compound

HRID 1352144Notes

Reaction equation

HRID 1352144 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[NH:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][CH:16]3[CH2:21][CH2:20][CH2:19][N:18]([CH:22]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:23]([OH:25])=O)[CH2:17]3)=[CH:12][CH:13]=2)[CH:8]=[N:7]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:3]([CH2:4][CH3:5])[C:23](=[O:25])[CH:22]([N:18]1[CH2:19][CH2:20][CH2:21][CH:16]([NH:15][C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][CH:12]=2)[NH:6][N:7]=[CH:8]3)[CH2:17]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH3:2]

Participants

8

Reactant 6

HCID 8021DiethylamineHCID 218852-DimethylaminopyridineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 17838237HCID 17838237, compound

Product 1

HCID 17838152HCID 17838152, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diethylamine (35 mg) and the compound prepared in Example 222 (88 mg) were dissolved in dimethylformamide (1 ml), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (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] to give 58 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]

Sources & evidence

ORD record
ord-444ad5182e3a423b8500e01e17af7e38
Source dataset
uspto-grants-2007_05
Patent number
US07217722B2

Reaction notes

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