tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate → 4-{4-[8-(2-Fluoro-3-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 472606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472606
Cl[C:2]1[N:19]=[C:5]2[C:6]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=3[F:18])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([C:33]2[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([C:33]2[CH:38]=[CH:37][C:36]([NH:39][C:2]3[N:19]=[C:5]4[C:6]([C:10]5[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=5[F:18])=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)=[CH:35][CH:34]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Komponenten

3

Edukt 2

HCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylateHCID 67481554HCID 67481554, Verbindung

Produkt 1

HCID 498396114-{4-[8-(2-Fluoro-3-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

Versuchsvorschrift

4-{4-[8-(2-Fluoro-3-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester was prepared from 2-chloro-8-(2-fluoro-3-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridine (0.248 g, 0.893 mmol) and 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.296 g, 1.07 mmol) in a manner analogous to Example 311a and 311b to give product (0.312 g, 67%). MP=98-102° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.63 (s, 1H), 8.83 (d, 1H), 7.60 (m, 3H), 7.25 (m, 3H), 7.10 (m, 3H), 4.05 (m, 2H), 3.90 (s, 3H), 2.80 (br m, 2H), 2.60 (m, 1H), 1.45 (m, 2H), 1.75 (m, 2H), 1.41 (s, 9H). MS=518 (MH)+.

Quellen und Nachweise

ORD-Eintrag
ord-6d25b465be6f4c308dc9d9d8404bd57b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633173B2

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