Methanol → 6-Chloro-4-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-1,2,4-benzotriazin-3(4H)-one 1-oxide

HRID 255370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 255370
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:15]3[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=3[N+:13]([O-:21])=[N:12][C:11]2=[O:22])[CH2:4][CH2:3]1.[O:23]1[C:32]2[CH:31]=[C:30]([CH:33]=O)[N:29]=[CH:28][C:27]=2[O:26][CH2:25][CH2:24]1.C(O[BH3-])(=O)C.[Na+].CO>ClCCl.C(O)(=O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]2[N+:13]([O-:21])=[N:12][C:11](=[O:22])[N:10]([CH2:9][CH2:8][N:5]3[CH2:4][CH2:3][CH:2]([NH:1][CH2:33][C:30]4[N:29]=[CH:28][C:27]5[O:26][CH2:25][CH2:24][O:23][C:32]=5[CH:31]=4)[CH2:7][CH2:6]3)[C:15]=2[CH:16]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 23670382SodiumacetoxyborohydrideHCID 866426604-[2-(4-Aminopiperidin-1-yl)ethyl]-6-chloro-1,2,4-benzotriazin-3(4H)-one 1-oxide2×

Produkt 1

HCID 250310676-Chloro-4-(2-{4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]piperidin-1-yl}ethyl)-1,2,4-benzotriazin-3(4H)-one 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-chloro-1,2,4-benzotriazin-3(4H)-one 1-oxide (Intermediate 205, (0.25 g) was reacted with 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde (WO 2004/058144) (0.14 g) and sodium acetoxyborohydride (0.34 g) as described for Example 107. Chromatography on silica gel with 0-20% methanol in dichloromethane gave 60 mg of the title compound as acetic acid salt (0.37 g).

Quellen und Nachweise

ORD-Eintrag
ord-a0bc2c2659354527931886d1919054ae
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875715B2

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