Diisopropylethylamine → 3-amino-N-(5-chloro-2-methylbenzyl)isoxazole-5-carboxamide

HRID 1891411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1891411
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=O)[O:4][N:3]=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.[Cl:37][C:38]1[CH:39]=[CH:40][C:41]([CH3:46])=[C:42]([CH2:44][NH2:45])[CH:43]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C.O>[NH2:1][C:2]1[CH:6]=[C:5]([C:7]([NH:45][CH2:44][C:42]2[CH:43]=[C:38]([Cl:37])[CH:39]=[CH:40][C:41]=2[CH3:46])=[O:9])[O:4][N:3]=1

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27576735-Chloro-2-methylbenzylamineHCID 552646873-Aminoisoxazole-5-carboxylic acid

Produkt 1

HCID 583322153-amino-N-(5-chloro-2-methylbenzyl)isoxazole-5-carboxamideAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-aminoisoxazole-5-carboxylic acid (492 mg, 3.84 mmol) in DMF (16 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.87 g, 4.22 mmol) at 0° C. The resulting solution was stirred for 5 min, after which time, 1-(5-chloro-2-methylphenyl)methanamine (598 mg, 3.84 mmol) and N,N-diisopropylethylamine (2.0 mL, 12 mmol) was added. The solution was stirred at room temperature for 0.5 h. The reaction solution was diluted with ethyl acetate and water, the organic layer was separated and dried over Na2SO4, filtered and concentrated. The residue was recrystallized with ethyl acetate and hexanes to give product (730 mg, 71%). LCMS calculated for C12H13ClN3O2(M+H)+: m/z=266.1.

Aufarbeitung

  1. stirringThe solution was stirred at room temperature for 0.5 h
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was recrystallized with ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5dbc5b1bf85b414a913153aa730ff024
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507541B2

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