1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59347371, compound

HRID 2366528Notes

Reaction equation

HRID 2366528 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([C:15]#[C:16][C:17]([OH:19])=O)(=[O:14])=[O:13])[CH:6]=[CH:5]2.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH:41]1[CH2:46][CH2:45][CH:44]([N:47]2[CH2:51][CH2:50][CH2:49][C:48]2=[O:52])[CH2:43][CH2:42]1>CN(C=O)C.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([CH2:15][CH2:16][C:17]([N:41]1[CH2:42][CH2:43][CH:44]([N:47]3[CH2:51][CH2:50][CH2:49][C:48]3=[O:52])[CH2:45][CH2:46]1)=[O:19])(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 183142501-(Piperidin-4-yl)pyrrolidin-2-oneHCID 1317281983-((6-Chloronaphthalen-2-yl)sulfonyl)propinoic acid

Product 1

HCID 59347371HCID 59347371, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

After 3-((6-chloronaphthalen-2-yl)sulfonyl)propinoic acid (0.30 g), HOBt (0.23 g) and WSC (0.29 g) were dissolved in DMF (10 mL), 1-(piperidin-4-yl)-2-pyrrolidinone (0.17 g) and triethylamine (0.10 g) were added thereto, and the mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, and diluted with ethyl acetate and an aqueous sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=10/1) to obtain the title compound (0.17 g, 39%) as a colorless powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-80a3f217343d45e4abbecbc0ddd70f76
Source dataset
uspto-grants-2014_04
Patent number
US08697865B2

Reaction notes

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