1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21952920, compound

HRID 1992727Notes

Reaction equation

HRID 1992727 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[N:26])[CH2:20][CH2:19][N:18]([CH2:21][C:22](O)=[O:23])[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N=C=NCCCN(C)C)C.ON1[C:43]2C=CC=[CH:47][C:42]=2[N:41]=N1.[CH3:48][O:49]C(ON)(C)C>C(OCC)(=O)C.CN(C)C=O>[CH3:43][C:42]([NH:41][C:22](=[O:23])[CH2:21][N:18]1[CH2:17][CH2:16][C:15]([C:9]2[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[CH:8]=2)([C:25]#[N:26])[CH2:20][CH2:19]1)([O:49][CH3:48])[CH3:47]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 10133035HCID 10133035, compoundHCID 13608208O-(2-Methoxyisopropyl)hydroxylamine

Product 1

HCID 21952920HCID 21952920, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (239 mg) prepared in Example 2, 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDC; 192 mg), 1-hydroxybenzotriazole (HOBt; 135 mg), dimethylformamide (4 ml) and (1-methoxy-1-methylethyl)oxyamine (0.35 ml) was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate, washed with water (twice), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→ethyl acetate alone) to thereby obtain the title compound (289 mg) having the following physical properties.

Workup

  1. washwashed with water (twice),
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-df79b17eeab94e7cb702f9c63ea97d22
Source dataset
uspto-grants-2010_01
Patent number
US07649095B2

Reaction notes

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