Hydrochloric Acid → 5-({[(2,4-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-[4-(4,5-dihydro-1H-imidazol-2-yl)benzyl]-N-methylfuran-3-carboxamide

HRID 468999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 468999
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([N:12]([CH2:14][C:15]1[O:19][CH:18]=[C:17]([C:20](O)=[O:21])[CH:16]=1)[CH3:13])(=[O:11])=[O:10].C1N=CN(C(N2C=NC=C2)=O)C=1.[NH:35]1[CH2:39][CH2:38][N:37]=[C:36]1[C:40]1[CH:45]=[CH:44][C:43]([CH2:46][NH:47][CH3:48])=[CH:42][CH:41]=1.Cl>ClCCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([N:12]([CH2:14][C:15]1[O:19][CH:18]=[C:17]([C:20]([N:47]([CH2:46][C:43]2[CH:44]=[CH:45][C:40]([C:36]3[NH:37][CH2:38][CH2:39][N:35]=3)=[CH:41][CH:42]=2)[CH3:48])=[O:21])[CH:16]=1)[CH3:13])(=[O:10])=[O:11]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 552648631-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylmethanamineHCID 583932675-({[(2,4-Dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid

Produkt 1

HCID 461754515-({[(2,4-dichlorophenyl)sulfonyl](methyl)amino}methyl)-N-[4-(4,5-dihydro-1H-imidazol-2-yl)benzyl]-N-methylfuran-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

5-({[(2,4-dichlorophenyl)sulfonyl](methyl)amino}methyl)furan-3-carboxylic acid (34 mg, 0.08 mmol) was dissolved in DCE (1 mL) and CDI (26 mg, 0.16 mmol) was added. The reaction was stirred for 2 h. The activated acid solution in DCE was added to a vial containing 1-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-N-methylmethanamine.HCl (41 mg, 0.16 mmol) and TEA (0.022 mL, 0.16 mmol). The reaction was stirred at ambient temperature for 18 h, then partitioned between saturated aqueous NaHCO3 (1 mL) and DCE (3×1 mL)). The organic layer was dried over MgSO4 and solvents were removed in vacuo. A portion of the crude was product purified using prep method A.

Aufarbeitung

  1. stirringThe reaction was stirred at ambient temperature for 18 h
  2. custompartitioned between saturated aqueous NaHCO3 (1 mL) and DCE (3×1 mL))
  3. dry with materialThe organic layer was dried over MgSO4 and solvents
  4. customwere removed in vacuo
  5. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-5d97f9220ae548b086e45e045135f275
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623859B2

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