1,2-Dichloroethane → N-{2-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]ethyl}-3-methoxy-N-methylterephthalamic Acid Methyl Ester

HRID 13864

Reaktionsgleichung

Reaktionsgleichung von HRID 13864
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([O:13][CH3:14])[CH:5]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:39][NH:40][CH2:41][CH2:42][N:43]1[CH2:48][CH2:47][CH:46]([O:49][C:50](=[O:64])[NH:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=2[C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[CH2:45][CH2:44]1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([N:40]([CH2:41][CH2:42][N:43]2[CH2:44][CH2:45][CH:46]([O:49][C:50](=[O:64])[NH:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=3[C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[CH2:47][CH2:48]2)[CH3:39])=[O:10])=[C:6]([O:13][CH3:14])[CH:5]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 566436031-(2-(Methylamino)ethyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamateHCID 593403342-Methoxy-4-(methoxycarbonyl)benzoic acid

Produkt 1

HCID 59340332N-{2-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]ethyl}-3-methoxy-N-methylterephthalamic Acid Methyl EsterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-methoxyterephthalic acid 4-methyl ester (450 mg, 2.1 mmol; prepared as described in Preparation 18) in DMF (10 mL) was added EDC (630 mg, 3.3 mmol), HOAt (2.4 mL, 1.18 mmol, 0.5M in DMF) and DIPEA (1.3 mL, 7.05 mmol). When the mixture was homogenous, a solution of biphenyl-2-ylcarbamic acid 1-(2-methylaminoethyl)piperidin-4-yl ester (830 mg, 2.4 mmol; prepared as described in Preparation 4) was added slowly. The reaction mixture was stirred at room temperature for 16 hours and then washed with water (100 mL), 1N HCl (100 mL), 1N NaOH (100 mL), brine (100 mL), dried over MgSO4, filtered and concentrated to afford the title intermediate in 89% yield (1.04 g, 1.9 mmol). MS m/z: [M+H+] calcd for C31H35N3O6, 545.6; found, 546.6.

Aufarbeitung

  1. washwashed with water (100 mL), 1N HCl (100 mL), 1N NaOH (100 mL), brine (100 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c96354509dec4955bc0831af79a7db73
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728144B2

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