Sodium Bicarbonate → (4R)-4-[(4-{[(7-Chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Hydrochloride

HRID 15358

Reaktionsgleichung

Reaktionsgleichung von HRID 15358
[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.[Cl:23][C:24]1[C:33]([CH:34]=O)=[N:32][C:31]2[NH:30][C:29](=[O:36])[CH2:28][O:27][C:26]=2[CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C(=O)(O)[O-].[Na+]>ClCCl.CO>[ClH:23].[Cl:23][C:24]1[C:33]([CH2:34][NH:1][CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]3[C:13]4=[C:14]([F:22])[CH:15]=[N:16][C:17]5[CH:18]=[CH:19][C:20](=[O:21])[N:11]([C:12]=54)[CH2:10]3)[CH2:4][CH2:3]2)=[N:32][C:31]2[NH:30][C:29](=[O:36])[CH2:28][O:27][C:26]=2[CH:25]=1

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 2724942TriacetoxyborohydrideHCID 574868727-Chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carbaldehydeHCID 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 68684679(4R)-4-[(4-{[(7-Chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-6-yl)methyl]amino}-1-piperidinyl)methyl]-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of (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, 016 mmol) and 7-chloro-3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine-6-carboxaldehyde (for a synthesis see WO2003064421, Example 15(c) (33 mg, 0.16 mmol) in anhydrous dichloromethane (1.5 mL) and anhydrous methanol (0.1 mL) was treated with triacetoxyborohydride (105 mg, 0.49 mmol). After 16 hours, an aqueous solution of sodium bicarbonate was added. The free base of the title compound came out of solution and was isolated by filtration, washed with water and dried in vacuo (50 mg, 60%).

Quellen und Nachweise

ORD-Eintrag
ord-227e0690a15443a9b364ea0c110396ff
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732461B2

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