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Dichloromethane → (racemic) N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-6-(1-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

HRID 1777994
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1777994
F.N1C=CC=CC=1.[Si]([O:15][CH:16]([C:18]1[CH:19]=[C:20]2[C:25](=[N:26][C:27]=1[CH:28]([O:31][CH3:32])[O:29][CH3:30])[N:24]([C:33]([NH:35][C:36]1[CH:41]=[C:40]([NH:42][CH2:43][CH2:44][O:45][CH3:46])[C:39]([C:47]#[N:48])=[CH:38][N:37]=1)=[O:34])[CH2:23][CH2:22][CH2:21]2)[CH3:17])(C(C)(C)C)(C)C.C([O-])(O)=O.[Na+].C(Cl)Cl>C1COCC1>[C:47]([C:39]1[C:40]([NH:42][CH2:43][CH2:44][O:45][CH3:46])=[CH:41][C:36]([NH:35][C:33]([N:24]2[C:25]3[C:20](=[CH:19][C:18]([CH:16]([OH:15])[CH3:17])=[C:27]([CH:28]([O:31][CH3:32])[O:29][CH3:30])[N:26]=3)[CH2:21][CH2:22][CH2:23]2)=[O:34])=[N:37][CH:38]=1)#[N:48]
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Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 64774Pyridine, hydrofluoride (1:1)HCID 516892Sodium BicarbonateHCID 131734796(racemic) 6-(1-((tert-butyldimethylsilyl)oxy)ethyl)-N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide2×

Produkt 1

HCID 118036612
(racemic) N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-6-(1-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Pyridine hydrofluoride (0.130 ml, 1.012 mmol) was added to a suspension of (racemic) 6-(1-((tert-butyldimethylsilyl)oxy)ethyl)-N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 184, 296 mg, 0.506 mmol) in THF (2.5 ml) and stirred for 18 h. The reaction mixture was poured into saturated aqueous NaHCO3 and DCM was added. Phases were separated and the water phase was back extracted with DCM (3×). Organic phases were combined, dried using Na2SO4, filtered and concentrated. The crude product was purified using silica gel column chromatography eluting with MeOH (0-4%) in DCM to yield the title compound as a colorless solid. (UPLC-MS 3) tR 0.90 min, ESI-MS 471.2 [M+H]+. 1H NMR (600 MHz, DMSO-d6) δ 13.62 (s, 1H), 8.27 (s, 1H), 7.84 (s, 1H), 7.53 (s, 1H), 6.92 (t, 1H), 5.45 (s, 1H), 5.23-5.16 (m, 2H), 3.98-3.88 (m, 2H), 3.53 (t, 2H), 3.41-3.31 (m, 8H), 3.30 (s, 3H), 2.89-2.83 (m, 2H), 1.95-1.86 (m, 2H), 1.30 (d, 3H).

Aufarbeitung

  1. additionwas added
  2. customPhases were separated
  3. extractionthe water phase was back extracted with DCM (3×)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified
  8. washeluting with MeOH (0-4%) in DCM

Quellen und Nachweise

ORD-Eintrag
ord-482fb60b4f85448194254ae78ed9b3b5
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09266883B2

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