Isopropylamine → tert-Butyl 3-(4-(5-(5-chloro-6-isopropylaminopyridin-3-yl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)propanoate

HRID 1820991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1820991
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:16][C:15]=3[CH3:29])[N:10]=2)[CH:5]=[N:6][C:7]=1Cl.[CH3:30][CH:31]([NH2:33])[CH3:32]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])=[CH:16][C:15]=3[CH3:29])[N:10]=2)[CH:5]=[N:6][C:7]=1[NH:33][CH:31]([CH3:32])[CH3:30]

Komponenten

4

Edukt 2

HCID 6363IsopropylamineHCID 86623617Tert-butyl 3-(4-(5-(5,6-dichloropyridin-3-yl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)propanoate

Produkt 1

HCID 68895002tert-Butyl 3-(4-(5-(5-chloro-6-isopropylaminopyridin-3-yl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)propanoateAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 31 mg (0.07 mmol) of tert-butyl 3-(4-(5-(5,6-dichloropyridin-3-yl)-1,2,4-oxadiazol-3-yl)-3-methylphenyl)propanoate (from EXAMPLE 15, Step A) and 120 μL (1.4 mmol) of 2-propylamine in 5.0 mL of THF was heated to 100° C. in a sealed tube overnight. The mixture was cooled to rt and concentrated. Chromatography on a Biotage 40S cartridge using 1:9 v/v Et2O/hexanes as the eluant gave 28 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.32 (d, J=6.4, 6H), 1.43 (s, 9H), 2.57 (t, J=7.7, 2H), 2.64 (s, 3H), 2.94 (t, J=7.7, 2H), 4.41 (m, 1H), 5.32 (d, J=7.5, 1H), 7.16-7.17 (m, 2H), 7.99 (d, J=8.5, 1H), 8.18 (d, J=1.8, 1H), 8.85 (d, J=1.8, 1H).

Aufarbeitung

  1. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2be2b3c5c78e4561b3dbce90dfc9b50d
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07605171B2

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