1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59190217, compound

HRID 1645271Notes

Reaction equation

HRID 1645271 reaction equation
[C:1]([C:4]1[O:8][C:7]([C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=2)[C:12]([OH:14])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=[C:31]=[N:32][CH2:33][CH2:34][CH2:35][N:36]([CH3:38])[CH3:37].CN1CCCNCC1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:37][N:36]1[CH2:35][CH2:34][CH2:33][N:32]([C:12]([C:11]2[CH:10]=[C:9]([C:7]3[O:8][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=3)[CH:17]=[CH:16][CH:15]=2)=[O:14])[CH2:31][CH2:38]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2283491-MethylhomopiperazineHCID 59190192HCID 59190192, compound

Product 1

HCID 59190217HCID 59190217, compoundYield 109%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(5-acetylfuran-2-yl)benzoic acid (1.10 g, 4.78 mmol) and HOBt (1.29 g, 9.56 mmol) in DMF (10 mL) was added EDCI (1.83 g, 9.56 mmol). The reaction was stirred at rt for 10 min and then added 1-methylhomopiperazine (2.38 mL, 19.12 mmol) followed by DIEA (3.35 mL, 19.12 mmol). The reaction mixture was stirred at rt for 1 h and diluted with H2O (50 mL). The mixture was extracted with DCM (3×50 mL), dried over Na2SO4 and concentrated to give brown oil (1.70 g). LCMS (ES): m/z 442 [M+1]+.

Workup

  1. stirringThe reaction mixture was stirred at rt for 1 h
  2. extractionThe mixture was extracted with DCM (3×50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d4a9aaa115ff4cfbbbaacd9471d45a53
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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