HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Chloroform → 3-Fluoro-4-({(3R,4S)-4-[(3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethyl)amino]-3-hydroxy-1-piperidinyl}methyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Hydrochloride
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Chloroform | HCID 6212 | — |
| Edukt | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Edukt | 3,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde | HCID 56640311 | — |
| Edukt | trans-4-(Boc-amino)-3-hydroxypiperidine | HCID 57525698 | — |
| Edukt | 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one | HCID 68686175 | — |
| Lösungsmittel | Methanol | HCID 887 | — |
| Produkt | 3-Fluoro-4-({(3R,4S)-4-[(3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethyl)amino]-3-hydroxy-1-piperidinyl}methyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Hydrochloride | HCID 68686877 | 70% |
Reaktionsschritte
A mixture of 4-{[(3R,4S)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one Diastereomer 1 (54 mg), 3,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde (for a synthesis see WO2004058144, Example 126(c)) (20.6 mg) and 3A molecular sieves in chloroform (1 ml) and methanol (1 ml) was heated at 65° C. for 5 h, cooled and then sodium triacetoxyborohydride (53 mg) was added. The general procedure of Example 72 was then followed to obtain the free base of the title compound (41 mg, 70%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07732461B2 |
| Quelldatensatz | uspto-grants-2010_06 |
| ORD ID | ord-5c694ce8a0b14c81a0674c18c4f5849b |
| Quellennotiz | uspto-grants-2010_06 |