Diisopropylethylamine → HCID 46941027, Verbindung

HRID 2354357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354357
[CH3:1][C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:5]2[N:6]([CH2:10][C:11]([OH:13])=O)[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[C:54]1([C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)[CH:59]=[CH:58][C:57]([CH:60]([NH:67][CH3:68])[CH2:61][N:62]2[CH2:66][CH2:65][CH2:64][CH2:63]2)=[CH:56][CH:55]=1>C(Cl)Cl>[C:54]1([C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=2)[CH:59]=[CH:58][C:57]([CH:60]([N:67]([CH3:68])[C:11](=[O:13])[CH2:10][N:6]2[C:5]3[CH:14]=[C:15]([O:16][CH3:17])[C:2]([CH3:1])=[CH:3][C:4]=3[O:8][C:7]2=[O:9])[CH2:61][N:62]2[CH2:66][CH2:65][CH2:64][CH2:63]2)=[CH:56][CH:55]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2756716(1-Biphenyl-4-yl-2-pyrrolidin-1-yl-ethyl)-methyl-amineHCID 57457148[6-Methyl-5-(methyloxy)-2-oxo-1,3-benzoxazol-3(2H)-yl]acetic acid

Produkt 1

HCID 46941027HCID 46941027, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

[6-Methyl-5-(methyloxy)-2-oxo-1,3-benzoxazol-3(2H)-yl]acetic acid (59 mg, 0.25 mmol) and BOP reagent (133 mg, 0.30 mmol) were dissolved in CH2Cl2 (1 mL), and diisopropylethylamine (32 mg, 0.25 mmol) was added to it. The resulting mixture was stirred at room temperature for 5 min, then 1-(4-biphenylyl)-N-methyl-2-(1-pyrrolidinyl)ethanamine (70 mg, 0.25 mmol) was added. Stirring was continued for 16 h and then the mixture was concentrated. The residue was dissolved in CH3OH, and purified by preparative HPLC (YMC CombiPrep ODS-A, 50×50 mm, 50 mL/min, A: acetonitrile B: water with NH4OH at pH=10, A: 20% to 70% during 12 min, UV detection at 214 nm) to give 92 mg (74%) of the title compound as a white solid. MS (ES) m/e 500 [M+H]+.

Aufarbeitung

  1. stirringStirring
  2. waitwas continued for 16 h
  3. concentrationthe mixture was concentrated
  4. dissolutionThe residue was dissolved in CH3OH
  5. custompurified by preparative HPLC (YMC CombiPrep ODS-A, 50×50 mm, 50 mL/min
  6. waitA: acetonitrile B: water with NH4OH at pH=10, A: 20% to 70% during 12 min

Quellen und Nachweise

ORD-Eintrag
ord-9d1bd7557b644e1cb97e5d5efac0f14f
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749998B2

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