1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59190116, compound

HRID 1645274Notes

Reaction equation

HRID 1645274 reaction equation
[C:1]([C:4]1[O:8][C:7]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)=[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:13]([C:12]2[CH:11]=[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]=2)=[O:15])[CH2:31][CH2:38]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2283491-MethylhomopiperazineHCID 59190188HCID 59190188, compound

Product 1

HCID 59190116HCID 59190116, compoundYield 113%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(5-acetylfuran-2-yl)benzoic acid (500 g, 2.17 mmol) and HOBt (587 mg, 4.35 mol) in DMF (5 mL) was added EDCI (835 mg, 4.35 mmol). The reaction was stirred at rt for 10 min and then 1-methylhomopiperazine (1.08 mL, 8.69 mol) was added, followed by DIEA (1.52 mL, 8.69 mmol). The reaction mixture was stirred at rt for 3 h and diluted with H2O (20 mL). The mixture was extracted with DCM (3×25 mL), washed with water (2×25 mL) then brine (25 mL), dried over Na2SO4 and concentrated to give brown oil (800 mg). LCMS (ES): m/z 442 [M+1]+.

Workup

  1. stirringThe reaction mixture was stirred at rt for 3 h
  2. extractionThe mixture was extracted with DCM (3×25 mL)
  3. washwashed with water (2×25 mL)
  4. dry with materialbrine (25 mL), dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d9b866f9ccee4c3ab5deb7f6c79b417a
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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