Diisopropylethylamine → N-{(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-phenylpropan-2-yl}-5-methyl-[1,3,4]oxadiazol-2-carboxamide

HRID 13142

Reaktionsgleichung

Reaktionsgleichung von HRID 13142
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[K+].[CH3:35][C:36]1[O:40][C:39]([C:41]([O-:43])=O)=[N:38][N:37]=1.[F:44][C:45]1[CH:50]=[CH:49][C:48]([N:51]2[C:59]3[C:54](=[CH:55][C:56]([O:60][C@@H:61]([C:65]4[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=4)[C@H:62]([NH2:64])[CH3:63])=[CH:57][CH:58]=3)[CH:53]=[N:52]2)=[CH:47][CH:46]=1>CN(C=O)C.ClCCl>[F:44][C:45]1[CH:46]=[CH:47][C:48]([N:51]2[C:59]3[C:54](=[CH:55][C:56]([O:60][C@H:61]([C:65]4[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=4)[C@@H:62]([NH:64][C:41]([C:39]4[O:40][C:36]([CH3:35])=[N:37][N:38]=4)=[O:43])[CH3:63])=[CH:57][CH:58]=3)[CH:53]=[N:52]2)=[CH:49][CH:50]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24820502Potassium 5-methyl-1,3,4-oxadiazole-2-carboxylateHCID 66812640(1S,2R)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-phenylpropan-2-amine

Produkt 1

HCID 59339738N-{(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-phenylpropan-2-yl}-5-methyl-[1,3,4]oxadiazol-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of HATU (630 mg, 1.66 mmol) in DMF (1 ml) was added ethyldiisopropylamine (570 μl, 3.3 mmol), followed by 5-methyl-[1,3,4]oxadiazol carboxylic acid potassium salt (138 mg, 830 μmol) and stirred for 20 min. Then (1S,2R)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-phenylpropan-2-amine (300 mg, 830 mmol) in DMF (1 ml) was added to the brown/red solution and the stirring was continued for 24 h at r.t. The mixture was diluted by dichloromethane and filtrated through a path of silica gel. Solvent was removed under reduced pressure, and the residue was purified by preparative TLC on silica gel (hexane/acetone 50%). Yield 82 mg (21%).

Aufarbeitung

  1. waitthe stirring was continued for 24 h at r.t
  2. filtrationfiltrated through a path of silica gel
  3. customSolvent was removed under reduced pressure
  4. customthe residue was purified by preparative TLC on silica gel (hexane/acetone 50%)

Quellen und Nachweise

ORD-Eintrag
ord-babf09e2a6cc4b8f9f708906304baa0d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

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