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)-N,2-dimethylfuran-3-carboxamide

HRID 469028

Reaction equation

HRID 469028 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][C:19]([CH3:21])=[C:18]([C:22]([OH:24])=O)[CH:17]=2)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:25])[CH:4]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH:38]1[CH2:42][CH2:41][N:40]=[C:39]1[C:43]1[CH:48]=[CH:47][C:46]([CH2:49][CH2:50][NH:51][CH3:52])=[CH:45][CH:44]=1.CCN(C(C)C)C(C)C>ClCCCl.CN(C=O)C>[NH:40]1[CH2:41][CH2:42][N:38]=[C:39]1[C:43]1[CH:44]=[CH:45][C:46]([CH2:49][CH2:50][N:51]([CH3:52])[C:22]([C:18]2[CH:17]=[C:16]([CH2:15][N:13]([S:10]([C:6]3[C:5]([CH3:25])=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=3[CH3:9])(=[O:11])=[O:12])[CH3:14])[O:20][C:19]=2[CH3:21])=[O:24])=[CH:47][CH:48]=1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 583929725-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-2-methylfuran-3-carboxylic acidHCID 672171912-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylethanamine

Product 1

HCID 58393419N-{2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]ethyl}-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N,2-dimethylfuran-3-carboxamide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-2-methylfuran-3-carboxylic acid (82 mg, 0.22 mmol) was dissolved in DCE (1 mL) and CDI (72 mg, 0.33 mmol) was added. The reaction was stirred at ambient temperature for 2 h and 0.5 mL of this solution was added to a flask containing 2-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylethanamine 0.3 HCl (34 mg, 0.11 mmol) and DIPEA (0.076 mL, 0.44 mmol) in DMF (2 mL). The reaction was stirred at ambient temperature for 3 days, then heated in a microwave at 120° C., 250 psi, 200 W for 2×20 min. The reaction was concentrated and diluted with DCM, then washed with water and saturated brine, and dried over MgSO4. The filtrate was shaken with Ambersep and PL-MIA resins, then filtered. The solvent was removed in vacuo and a portion of the crude product purified using prep method C.

Workup

  1. stirringThe reaction was stirred at ambient temperature for 3 days
  2. temperatureheated in a microwave at 120° C.
  3. customfor 2×20 min
  4. concentrationThe reaction was concentrated
  5. additiondiluted with DCM
  6. washwashed with water and saturated brine
  7. dry with materialdried over MgSO4
  8. stirringThe filtrate was shaken with Ambersep and PL-MIA resins
  9. filtrationfiltered
  10. customThe solvent was removed in vacuo
  11. customa portion of the crude product purified

Sources & evidence

ORD record
ord-a528812d5d3046f09909b8624baa50b0
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Linked notes

Loading…