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

HRID 20215Notes

Reaction equation

HRID 20215 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 131728198HCID 131728198, compound

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-0f3d0ecf69574958ae540bf9fed29955
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Reaction notes

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