1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 90904917, compound

HRID 643071Notes

Reaction equation

HRID 643071 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C@@H:11]([CH3:14])[CH2:12][CH3:13])[CH2:7]C(O)=O)=[O:4].Cl.Cl.[CH2:17]([NH:24][NH2:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C.C1C=CC2N([OH:55])N=NC=2C=1>C1COCC1>[CH2:17]([NH:24][NH:25][C:7]([C@@H:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[C@@H:11]([CH3:14])[CH2:12][CH3:13])=[O:55])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 146540Benzylhydrazine dihydrochlorideHCID 86599729HCID 86599729, compound

Product 1

HCID 90904917HCID 90904917, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of Example 3A (3.32 g, 17.5 mmol) in THF (70 mL) was treated with benzylhydrazine di-HCl salt (3.42 g, 1 equivalent), diisopropylethyl amine (9.2 mL, 3 equivalents), EDAC (6.05 g, 1.8 equivalents), and HOBT (3.56 g, 1.5 equivalents), and stirred at 25° C. for 16 hrs. The solvents were evaporated, and the crude residue was partitioned between chloroform and 10% sodium bicarbonate. The organic layer was separated, washed with 10% sodium bicarbonate, brine, dried over sodium sulfate, filtered and the solvents were evaporated. The crude residue was purified using 1% methanol/chloroform to give 2.41 g (47%) of the title compound.

Workup

  1. customThe solvents were evaporated
  2. customthe crude residue was partitioned between chloroform and 10% sodium bicarbonate
  3. customThe organic layer was separated
  4. washwashed with 10% sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvents were evaporated
  8. customThe crude residue was purified

Sources & evidence

ORD record
ord-7cff39c88eeb428dbb29db32ccbb4d3b
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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