Trimethylamine → 3-{4-[3-(2-Cyanophenoxy)phenyl]-2-oxo-pyrrolidin-1-yl}benzamide

HRID 1727151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727151
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:12][N:11]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=3)[C:16]([NH2:18])=[O:17])[C:10](=[O:22])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O)#[N:24].N(C)(C)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:12][N:11]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=3)[C:16]([NH2:18])=[O:17])[C:10](=[O:22])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1)#[N:24]

Komponenten

6

Edukt 3

HCID 1146TrimethylamineHCID 27346102-Cyanophenylboronic acidHCID 688283783-[4-(3-Hydroxyphenyl)-2-oxo-pyrrolidin-1-yl]benzamide

Produkt 1

HCID 688325043-{4-[3-(2-Cyanophenoxy)phenyl]-2-oxo-pyrrolidin-1-yl}benzamideAusbeute 43,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 3-[4-(3-hydroxyphenyl)-2-oxo-pyrrolidin-1-yl]benzamide (30 mg), 2-cyanobenzeneboronic acid (12 mg), and copper acetate (2 eq) was created in a dry tube. The mixture was dissolved in 2 mL CH2Cl2 followed by the addition of (CH3)3N (3 eq). The mixture was stirred at r.t. for 24 h, and then diluted with 10 mL CH2Cl2. The resulting mixture was filtered and washed with NH4Cl solution, water and brine. After removal of solvent, the residue was purified by preparative LC-MS to give 14 mg of the desired product. Yield: 35%.

Aufarbeitung

  1. customwas created in a dry tube
  2. filtrationThe resulting mixture was filtered
  3. washwashed with NH4Cl solution, water and brine
  4. customAfter removal of solvent
  5. customthe residue was purified by preparative LC-MS

Quellen und Nachweise

ORD-Eintrag
ord-918ee949fa84431ba3d6e6c5a2a6b387
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495016B2

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