Chloroform → (4R)-3-Fluoro-4-[(4-{[(2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazin-7-yl)methyl]amino}-1-piperidinyl)methyl]-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Hydrochloride

HRID 15346

Reaktionsgleichung

Reaktionsgleichung von HRID 15346
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]2[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.C(OC(=O)NC1CCNCC1O)(C)(C)C.[O:38]=[C:39]1[CH2:44][S:43][C:42]2[N:45]=[CH:46][C:47]([CH:49]=O)=[CH:48][C:41]=2[NH:40]1.C([BH3-])#N.[Na+].C(Cl)(Cl)[Cl:56]>CO>[ClH:56].[F:22][C:14]1[CH:15]=[N:16][C:17]2[CH:18]=[CH:19][C:20](=[O:21])[N:11]3[CH2:10][C@@H:9]([CH2:8][N:5]4[CH2:6][CH2:7][CH:2]([NH:1][CH2:49][C:47]5[CH:46]=[N:45][C:42]6[S:43][CH2:44][C:39](=[O:38])[NH:40][C:41]=6[CH:48]=5)[CH2:3][CH2:4]4)[C:13]=1[C:12]=23

Komponenten

7

Edukt 5

HCID 6212ChloroformHCID 5003444Sodium cyanoborohydrideHCID 218737332-Oxo-2,3-dihydro-1h-pyrido[2,3-b][1,4]thiazine-7-carbaldehydeHCID 57525698trans-4-(Boc-amino)-3-hydroxypiperidineHCID 68686964(4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

Produkt 1

HCID 68685581(4R)-3-Fluoro-4-[(4-{[(2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazin-7-yl)methyl]amino}-1-piperidinyl)methyl]-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one HydrochlorideAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(4R)-4-[(4-amino-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Enantiomer 1 (50 mg, 0.166 mmol) and 2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]thiazine-7-carboxaldehyde (for a synthesis see WO2004058144 Example 48(e)) (32 mg, 0.166 mol) were stirred in chloroform (1 mL) and methanol (1 mL) for 2 h at room temperature. Sodium cyanoborohydride (40 g) was added and the mixture was stirred for 18 h. The mixture was filtered and evaporated. Chromatography on silica, eluting with 0-20% methanol/dichloromethane, gave the free base of the title compound (31 mg, 39%).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. washChromatography on silica, eluting with 0-20% methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-25d14cde742e42cf8430f9c2f724e745
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732461B2

Verknüpfte Notizen

Wird geladen…