Diisopropylethylamine → 2-(2,6-Dichlorophenyl)-benzooxazole-6-carboxylic acid (2-o-tolyl-ethyl)-amide

HRID 1514971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514971
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[O:10][C:11]2[CH:17]=[C:16]([C:18]([OH:20])=O)[CH:15]=[CH:14][C:12]=2[N:13]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[C:57]1([CH3:66])[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[CH2:63][CH2:64][NH2:65]>CN(C=O)C>[C:57]1([CH3:66])[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[CH2:63][CH2:64][NH:65][C:18]([C:16]1[CH:15]=[CH:14][C:12]2[N:13]=[C:9]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])[O:10][C:11]=2[CH:17]=1)=[O:20]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 20638682-MethylphenethylamineHCID 53271602-(2,6-Dichlorophenyl)-1,3-benzoxazole-6-carboxylic acid

Produkt 1

HCID 251092472-(2,6-Dichlorophenyl)-benzooxazole-6-carboxylic acid (2-o-tolyl-ethyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 2-(2,6-dichloro-phenyl)-benzooxazole-6-carboxylic acid (8.9 mg) in anhydrous DMF (0.5 mL) was added BOP (17.4 mg), diisopropylethylamine (0.014 mL), and 2-o-tolyl-ethylamine (5.5 mg). The reaction mixture was stirred at 85° C. overnight, quenched with 1N NaOH aqueous solution at 0° C., extracted with EtOAc. The extracts were dried over Na2SO4 and concentrated in vacuo. The crude reaction mixture was purified by silica SPE eluting with EtOAc/Hexane to give 2-(2,6-dichlorophenyl)-benzooxazole-6-carboxylic acid (2-o-tolyl-ethyl)-amide: MS (m/z) 425.1 (M+1).

Aufarbeitung

  1. customquenched with 1N NaOH aqueous solution at 0° C.
  2. extractionextracted with EtOAc
  3. dry with materialThe extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude reaction mixture
  6. customwas purified by silica SPE
  7. washeluting with EtOAc/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-82076be12c4449a286c95c20edd76664
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

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