1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69935134, compound

HRID 2416649Notes

Reaction equation

HRID 2416649 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([NH:12][C@@H:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[C:14]([NH:16][CH2:17][C:18]([OH:20])=O)=[O:15])=[O:11])=[CH:7][C:6]=2[CH:28]=1.[C:29]1([N:35]2[CH2:40][CH2:39][NH:38][C@@H:37]([CH3:41])[CH2:36]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([NH:12][C@@H:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[C:14]([NH:16][CH2:17][C:18]([N:38]3[CH2:39][CH2:40][N:35]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:36][C@@H:37]3[CH3:41])=[O:20])=[O:15])=[O:11])=[CH:7][C:6]=2[CH:28]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27441130HCID 27441130, compoundHCID 69379173HCID 69379173, compound

Product 1

HCID 69935134HCID 69935134, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [[(2S)-2-[[(5-chloro-1-benzofuran-2-yl)carbonyl]amino]-3-(2-pyridyl)propanoyl]amino]acetic acid (150 mg), (S)-1-phenyl-3-methylpiperazine (79 mg), 1-hydroxy-benzotriazole (55 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (79 mg) in N,N-dimethylformamide (3 ml) was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (15 ml), and washed successively with saturated aqueous sodium hydrogencarbonate solution, water, and brine. The organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol 10:1) to give the title compound as a colorless amorphous solid.

Workup

  1. washwashed successively with saturated aqueous sodium hydrogencarbonate solution, water, and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform-methanol 10:1)

Sources & evidence

ORD record
ord-86aad1e3099446cc8de1d53d8aa5bb10
Source dataset
uspto-grants-2004_11
Patent number
US06825200B1

Reaction notes

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