(4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one → (4S)-4-[(4-amino-1-piperidinyl)methyl]-3,8-difluoro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

HRID 15140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15140
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@@:9]2([OH:23])[C:13]3=[C:14]([F: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][CH2:3]1.NC1CCN(C[C@]2(O)C3=C([F:45])C=NC4C=CC(=O)N(C=43)C2)CC1>>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:8][C@@:9]2([OH:23])[C:13]3=[C:14]([F:22])[CH:15]=[N:16][C:17]4[CH:18]=[C:19]([F:45])[C:20](=[O:21])[N:11]([C:12]=43)[CH2:10]2)[CH2:6][CH2:7]1

Komponenten

3

Edukt 2

HCID 23633344(4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one2×HCID 23634276(4s)-4-[(4-Amino-1-piperidinyl)methyl]-3-fluoro-4-hydroxy-4,5-dihydro-7h-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one2×

Produkt 1

HCID 23633410(4S)-4-[(4-amino-1-piperidinyl)methyl]-3,8-difluoro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

Versuchsvorschrift

A portion of this material (740 mg, estimated ratio of E1:E2 ca. 3:1) was resolved by preparative chiral HPLC into the two enantiomers E1 and E2, using a Chiralpak AD column, eluting with 50:50:0.1-CH3CN:isopropylalcohol:isopropylamine affording 553 mg of the desired E1 (4S) enantiomer (>99.5% ee) as the first eluting enantiomer.

Aufarbeitung

  1. washeluting with 50:50:0

Quellen und Nachweise

ORD-Eintrag
ord-e5dbd86921174380b7258f363d7a1301
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732460B2

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