2,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehyde → 3-Chloro-4-({(3r,4s)-4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-3-hydroxy-1-piperidinyl}methyl)-4,5-dihydro-7h-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one hydrochloride

HRID 15320

Reaktionsgleichung

Reaktionsgleichung von HRID 15320
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]2[C:13]3=[C:14]([Cl:22])[CH:15]=[N:16][C:17]4[CH:18]=[CH:19][C:20](=[O:21])[N:11]([C:12]=43)[CH2:10]2)[CH2:4][C@H:3]1[OH:23].[O:24]1[C:33]2[CH:32]=[C:31]([CH:34]=O)[N:30]=[CH:29][C:28]=2[O:27][CH2:26][CH2:25]1>>[ClH:22].[Cl:22][C:14]1[CH:15]=[N:16][C:17]2[CH:18]=[CH:19][C:20](=[O:21])[N:11]3[CH2:10][CH:9]([CH2:8][N:5]4[CH2:6][CH2:7][C@H:2]([NH:1][CH2:34][C:31]5[N:30]=[CH:29][C:28]6[O:27][CH2:26][CH2:25][O:24][C:33]=6[CH:32]=5)[C@H:3]([OH:23])[CH2:4]4)[C:13]=1[C:12]=23

Komponenten

3

Edukt 2

HCID 218736682,3-Dihydro[1,4]dioxino[2,3-c]pyridine-7-carbaldehydeHCID 68685696racemic 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

Produkt 1

HCID 686879423-Chloro-4-({(3r,4s)-4-[(2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)amino]-3-hydroxy-1-piperidinyl}methyl)-4,5-dihydro-7h-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one hydrochlorideAusbeute 58 %

Versuchsvorschrift

The free base of the title compound was synthesised from racemic 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-chloro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one and 2,3-dihydro[1,4]dioxino[2,3-c]pyridine-7-carboxaldehyde (for a synthesis see WO2004058144, Example 2(c)) according to the general method of Example 2(h), in 58% yield

Quellen und Nachweise

ORD-Eintrag
ord-a53814bab2544ef8aec776b8ce29f29e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732461B2

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