1,1'-Carbonyldiimidazole → N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxamide

HRID 468984Notes

Reaction equation

HRID 468984 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.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH:37]1[CH2:41][CH2:40][N:39]=[C:38]1[C:42]1[CH:47]=[CH:46][C:45]([CH2:48][CH2:49][NH2:50])=[CH:44][CH:43]=1.CCN(C(C)C)C(C)C>ClCCCl>[NH:39]1[CH2:40][CH2:41][N:37]=[C:38]1[C:42]1[CH:43]=[CH:44][C:45]([CH2:48][CH2:49][NH:50][C:21]([C:18]2[CH:17]=[C:16]([CH2:15][N:13]([S:10]([C:6]3[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH3:24])(=[O:12])=[O:11])[CH3:14])[O:20][CH:19]=2)=[O:22])=[CH:46][CH:47]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 223907052-[4-(4,5-Dihydro-1H-imidazol-2-yl)phenyl]ethan-1-amineHCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Product 1

HCID 46175898N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (100 mg, 0.3 mmol) was dissolved in DCE (6 mL) and CDI (195 mg, 0.6 mmol) was added. The reaction was stirred at room temperature until complete as determined by LCMS. 2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethanamine (54 mg, 0.3 mmol) and DIPEA (0.63 mL, 1.8 mmol) was added and the reaction stirred for 4 days. The reaction was washed with saturated aqueous NH4Cl (6 mL) and the aqueous wash extracted with DCE (3×6 mL). The combined organic extracts were dried over MgSO4 and the solvent removed in vacuo. The resulting crude product was purified using prep method B to afford the title compound.

Workup

  1. stirringthe reaction stirred for 4 days
  2. washThe reaction was washed with saturated aqueous NH4Cl (6 mL)
  3. washthe aqueous wash
  4. extractionextracted with DCE (3×6 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. customthe solvent removed in vacuo
  7. customThe resulting crude product was purified

Sources & evidence

ORD record
ord-248d55b2b763432d9eb6466fe0032e32
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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