Diisopropylethylamine → HCID 68443628, Verbindung

HRID 1911669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1911669
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C([N:49]([CH2:53]C)[CH:50]([CH3:52])[CH3:51])(C)C.NC1C[CH2:60][O:59][CH2:58]C1>CN(C=O)C>[CH3:53][N:49]([CH:50]1[CH2:51][CH2:60][O:59][CH2:58][CH2:52]1)[C:19](=[O:21])[C:18]1[CH:22]=[CH:23][C:15]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[N:16][CH:17]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 4192234-AminotetrahydropyranHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 665992136-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid

Produkt 1

HCID 68443628HCID 68443628, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (200 mg, 0.64 mmol) in DMF (2 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (228 mg, 0.71 mmol), N,N-diisopropyl ethyl amine (552 μL, 3.22 mmol) and 4-aminotetrahydropyran (0.77 mmol). The resulting reaction mixture was stirred for 12 h at ambient temperature. After dilution with ethyl acetate (20 mL) it was washed with water (20 mL) and aqueous sodium carbonate (saturated, 40 mL). The organic layer was dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate=80:20 to 20:80) afforded the title compound (231 mg, 91%) which was obtained as a white solid. MS: m/e=394.1 [M+H]+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. washAfter dilution with ethyl acetate (20 mL) it was washed with water (20 mL) and aqueous sodium carbonate (saturated, 40 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=80:20 to 20:80)

Quellen und Nachweise

ORD-Eintrag
ord-51a2b68303d94d57bf4de522513ac69a
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604062B2

Notizen zur Reaktion

Wird geladen…