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

HRID 469007Notes

Reaction equation

HRID 469007 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][NH:49][CH3:50])=[CH:44][CH:43]=1.CCN(C(C)C)C(C)C>ClCCCl.CN(C=O)C>[NH:39]1[CH2:40][CH2:41][N:37]=[C:38]1[C:42]1[CH:43]=[CH:44][C:45]([CH2:48][N:49]([CH3:50])[C:21]([C:18]2[CH:17]=[C:16]([CH2:15][N:13]([S:10]([C:6]3[C:5]([CH3:24])=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=3[CH3:9])(=[O:11])=[O:12])[CH3:14])[O:20][CH:19]=2)=[O:22])=[CH:46][CH:47]=1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 552648631-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylmethanamine2×HCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Product 1

HCID 58393008N-[4-(4,5-dihydro-1H-imidazol-2-yl)benzyl]-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-methylfuran-3-carboxamide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

5-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (30 mg, 0.09 mmol) was dissolved in DCE (2 mL) and CDI (30 mg, 0.18 mmol) added. The reaction was stirred at room temperature until complete as determined by LCMS. 1-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylmethanamine (32 mg, 0.17 mmol) and DIPEA (0.032 mL, 0.18 mmol) was added and the reaction stirred for 3 days at ambient temperature. A further 32 mg 1-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylmethanamine was added, followed by DMF (0.5 mL) and the reaction was stirred for 18 h. The reaction was washed with saturated aqueous NH4Cl (3×5 mL) and the organic layer dried over MgSO4, shaken with PL-MIA and Ambersep resins, and concentrated. A portion of the crude product was purified using prep method C.

Workup

  1. stirringthe reaction stirred for 3 days at ambient temperature
  2. stirringthe reaction was stirred for 18 h
  3. washThe reaction was washed with saturated aqueous NH4Cl (3×5 mL)
  4. dry with materialthe organic layer dried over MgSO4
  5. stirringshaken with PL-MIA and Ambersep resins
  6. concentrationconcentrated
  7. customA portion of the crude product was purified

Sources & evidence

ORD record
ord-ba1bab81392d46a7a44b8b705ed298e5
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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