1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21939768, compound

HRID 1242948Notes

Reaction equation

HRID 1242948 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])=[O:10])=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.CN(C1C=CC=CN=1)C.[CH:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][C:38]=1[C:47]1[N:51]=[C:50]([CH2:52][CH2:53][C:54](O)=[O:55])[O:49][N:48]=1>C(OCC)(=O)C.O.CN(C=O)C.C(N(CC)CC)C>[CH3:16][N:14]([CH3:15])[CH2:13][CH2:12][NH:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:54](=[O:55])[CH2:53][CH2:52][C:50]2[O:49][N:48]=[C:47]([C:38]3[CH:39]=[CH:40][C:41]4[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=4)[CH:37]=3)[N:51]=2)=[CH:7][CH:6]=1

Participants

9

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 10704226HCID 10704226, compoundHCID 21939830HCID 21939830, compound

Product 1

HCID 21939768HCID 21939768, compoundYield 35.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Aminophenyl)-N-[2-(dimethylamino)ethyl]acetamide (221 mg), WSC (249 mg), 1-hydroxybenzotrizole (199 mg), triethylamine (0.4 ml), and dimethylaminopyridine (244 mg) were added to a DMF (5 ml) solution of 3-[3-(2-naphthyl)-1,2,4-oxadiazol-5-yl]propionic acid (268 mg), which was stirred for 5 hours. The reaction mixture was poured into water, and extraction was conducted using ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution, dried over sodium sulfate, and then concentrated. The residue was recrystallized from methanol, to give the titled compound (166 mg).

Workup

  1. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-343e476c23d14e099535404109c734bc
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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