1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58393157, compound

HRID 469022Notes

Reaction equation

HRID 469022 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][CH:19]=[C:18]([C:21](O)=[O:22])[CH:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:24])[CH:4]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:46][NH:47][CH2:48][C:49]1[CH:54]=[CH:53][C:52]([C:55]2[N:56]([CH3:60])[CH:57]=[CH:58][N:59]=2)=[CH:51][CH:50]=1>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][C:16]2[O:20][CH:19]=[C:18]([C:21]([N:47]([CH3:46])[CH2:48][C:49]3[CH:50]=[CH:51][C:52]([C:55]4[N:56]([CH3:60])[CH:57]=[CH:58][N:59]=4)=[CH:53][CH:54]=3)=[O:22])[CH:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:24])[CH:4]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acidHCID 63975987HCID 63975987, compound

Product 1

HCID 58393157HCID 58393157, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (50 mg, 0.14 mmol) was dissolved in DMF (3 mL) and EDCI (32 mg, 0.17 mmol) and HOBt (23 mg, 0.17 mmol) were added. The resulting solution was stirred for 60 min prior to the addition of N-methyl-1-[4-(1-methyl-1H-imidazol-2-yl)phenyl]methanamine (31 mg, 0.17 mmol) dissolved in DMF (2 mL) and stirred at ambient temperature for 18 h. The reaction was diluted with EtOAc (20 mL) and washed with water, saturated aqueous NaHCO3, saturated brine, dried over Na2SO4 and concentrated in vacuo. The resulting oil was purified using prep method C.

Workup

  1. stirringstirred at ambient temperature for 18 h
  2. washwashed with water, saturated aqueous NaHCO3, saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was purified

Sources & evidence

ORD record
ord-98aa0aefe344466ca348da5bdca3aa8f
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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