Diisopropylethylamine → 4-(3-(5-methylpyridin-2-yloxy)benzylidene)-N-(3,4-dimethylisoxazol-5-yl)piperidine-1-carboxamide

HRID 1666408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666408
Cl.[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[C:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH:11]=2)=[N:7][CH:8]=1.[CH3:23][C:24]1[C:28]([CH3:29])=[C:27]([NH:30][C:31](=O)[O:32]C2C=CC=CC=2)[O:26][N:25]=1.NC1ON=C(C)C=1C.C(N(C(C)C)CC)(C)C>C(#N)C>[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[CH:16]=[C:17]2[CH2:22][CH2:21][N:20]([C:31]([NH:30][C:27]3[O:26][N:25]=[C:24]([CH3:23])[C:28]=3[CH3:29])=[O:32])[CH2:19][CH2:18]2)=[N:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 883175-Amino-3,4-dimethylisoxazoleHCID 53485970Phenyl (3,4-dimethylisoxazol-5-yl)carbamateHCID 668761665-Methyl-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine hydrochloride

Produkt 1

HCID 249644274-(3-(5-methylpyridin-2-yloxy)benzylidene)-N-(3,4-dimethylisoxazol-5-yl)piperidine-1-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

5-Methyl-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine hydrochloride (150 mg, 0.473 mmol, from Example 44, Step 5), phenyl 3,4-dimethylisoxazol-5-ylcarbamate (110 mg, 0.473 mmol, prepared according to the procedure described in Synthesis, 1997, 1189-1194 from 5-amino-3,4-dimethylisoxazole) and diisopropylethylamine (0.20 mL, 1.15 mmol) were combined in acetonitrile (5 mL) and stirred at room temperature. After 16 h, the reaction was concentrated and the residue was purified by silica gel chromatography (0-30% EtOAc:CH2Cl2) to afford the title compound (86 mg) as a foamy white solid. MS APCI M+ 419.3, 378.2, 281.3; 1H NMR (400 MHz, CD3OD) δ ppm 1.83 (s, 3H) 2.18 (s, 3H) 2.29 (s, 3H) 2.43 (td, J=5.86, 1.16 Hz, 2H) 2.55 (td, J=5.73, 1.20 Hz, 2H) 3.48-3.54 (m, 2H) 3.57-3.65 (m, 2H) 6.44 (s, 1H) 6.82-6.87 (m, 1H) 6.89-6.96 (m, 2H) 7.02-7.11 (m, J=7.60, 1.50, 1.06, 0.74 Hz, 1H) 7.35 (dd, J=8.77, 7.65 Hz, 1H) 7.61-7.69 (m, J=8.38, 2.46, 1.15, 0.45 Hz, 1H) 7.96 (td, J=1.60, 0.72 Hz, 1H).

Aufarbeitung

  1. concentrationthe reaction was concentrated
  2. customthe residue was purified by silica gel chromatography (0-30% EtOAc:CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-1b6d6009e7444e56b6bde9e5e4091304
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044052B2

Notizen zur Reaktion

Wird geladen…