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

HRID 468982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 468982
[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.[N:37]1([C:42]2[CH:47]=[CH:46][C:45]([CH2:48][NH:49][CH3:50])=[CH:44][CH:43]=2)[CH:41]=[CH:40][N:39]=[CH:38]1>C1COCC1.C(Cl)Cl>[N:37]1([C:42]2[CH:43]=[CH:44][C:45]([CH2:48][N:49]([CH3:50])[C:21]([C:18]3[CH:17]=[C:16]([CH2:15][N:13]([S:10]([C:6]4[C:7]([CH3:9])=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[CH3:24])(=[O:12])=[O:11])[CH3:14])[O:20][CH:19]=3)=[O:22])=[CH:46][CH:47]=2)[CH:41]=[CH:40][N:39]=[CH:38]1

Komponenten

6

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 71573711-(4-(1H-Imidazol-1-yl)phenyl)-N-methylmethanamineHCID 583930975-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Produkt 1

HCID 46175897N-[4-(1H-imidazol-1-yl)benzyl]-5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-N-methylfuran-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-({[(4-Methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (53 mg, 0.15 mmol) was dissolved in THF (0.5 mL) and CDI (24 mg, 0.15 mmol) added. The reaction was stirred for 2 h prior to addition of 1-[4-(1H-imidazol-1-yl)phenyl]-N-methylmethanamine (25 mg, 0.135 mmol). The reaction was stirred at ambient temperature for 3 days, and diluted with DCM (1 mL) and washed with 2M aqueous K2CO3 (1 mL). The organic layer was dried over MgSO4, the solvent removed in vacuo and a portion of the crude product purified using prep method A.

Aufarbeitung

  1. stirringThe reaction was stirred at ambient temperature for 3 days
  2. washwashed with 2M aqueous K2CO3 (1 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent removed in vacuo
  5. customa portion of the crude product purified

Quellen und Nachweise

ORD-Eintrag
ord-c22f1f906d0e413084ca3fdd6a26ea82
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623859B2

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