Diisopropylethylamine → N-Hydroxy-2-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acetamide

HRID 1245384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1245384
[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH2:24][CH:23]([CH2:25][C:26]([OH:28])=O)[O:22][N:21]=3)=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.F[P-](F)(F)(F)(F)F.[N:36]1([O:45][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.NO>CN(C=O)C>[OH:45][NH:36][C:26](=[O:28])[CH2:25][CH:23]1[O:22][N:21]=[C:20]([C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:12][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]([CH3:1])[CH:11]=3)=[CH:19][CH:18]=2)[CH2:24]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 443297Hydroxyamine hydrochlorideHCID 21911127{3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acetic acid

Produkt 1

HCID 9865240N-Hydroxy-2-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acetamideAusbeute 31,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The {3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acetic acid (0.15 g, 0.4 mmol) was combined with BOP (0.265 g, 0.6 mmol) and diisopropylethylamine (0.5 mL) in DMF (5 mL) under nitrogen atmosphere at room temperature. The reaction was stirred for 15 minutes, and then hydroxylamine hydrochloride (0.042 g, 0.6 mmol) was added. The reaction was stirred overnight, concentrated in vacuo, and triturated with water saturated KH2PO4 solution to give a precipitate. The crude product was purified by HPLC on a C-18 column eluting with an acetonitrile/water/TFA gradient to give the title compound (0.05 g, 25%) as an amorphous solid. MS found: (M+H)+=392.

Aufarbeitung

  1. stirringThe reaction was stirred overnight
  2. concentrationconcentrated in vacuo
  3. customtriturated with water saturated KH2PO4 solution
  4. customto give a precipitate
  5. customThe crude product was purified by HPLC on a C-18 column
  6. washeluting with an acetonitrile/water/TFA gradient

Quellen und Nachweise

ORD-Eintrag
ord-6ccbc202c1134e9a856dc8b5b8076f2b
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07125870B2

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