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

HRID 1777992
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1777992
CS(O[CH:6]([C:8]1[C:9]([CH:34]([O:37][CH3:38])[O:35][CH3:36])=[N:10][C:11]2[N:12]([C:18](=[O:33])[NH:19][C:20]3[CH:25]=[C:24]([NH:26][CH2:27][CH2:28][O:29][CH3:30])[C:23]([C:31]#[N:32])=[CH:22][N:21]=3)[CH2:13][CH2:14][CH2:15][C:16]=2[CH:17]=1)[CH3:7])(=O)=O.[CH3:39][NH2:40]>C(Cl)Cl.CN(C=O)C.O>[C:31]([C:23]1[C:24]([NH:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:25][C:20]([NH:19][C:18]([N:12]2[C:11]3[C:16](=[CH:17][C:8]([CH:6]([NH:40][CH3:39])[CH3:7])=[C:9]([CH:34]([O:37][CH3:38])[O:35][CH3:36])[N:10]=3)[CH2:15][CH2:14][CH2:13]2)=[O:33])=[N:21][CH:22]=1)#[N:32]
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Komponenten

6

Edukt 2

HCID 6329MethylamineHCID 118036849(Racemic) 1-(8-((5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)carbamoyl)-2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)ethyl methanesulfonate2×

Produkt 1

HCID 118036356(racemic) N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-6-(1-(methylamino)ethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of (racemic) 1-(8-((5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)carbamoyl)-2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)ethyl methanesulfonate (intermediate 182, 231 mg, 0.421 mmol) in DCM (8 ml) and DMF (0.5 ml) at 0° C. was added methylamine (2M in THF, 3 mL, 6.00 mmol). The reaction mixture was allowed to warm to room temperature and continued to stir over night. The reaction mixture was diluted with water and DCM, phases were separated and the water phase was 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 (including 3% NH3, 4-5%) in DCM to yield the title compound as a colorless solid. (UPLC-MS 3) tR 0.76 min, ESI-MS 484.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 13.70 (s, 1H), 8.18 (s, 1H), 8.09 (s, 1H), 7.55 (s, 1H), 5.42 (s, 1H), 5.25 (t, 1H), 4.80-4.70 (m, 1H), 4.11-3.93 (m, 2H), 3.62 (t, 2H), 3.52-3.42 (m, 8H), 3.39 (s, 3H), 2.99-2.81 (m, 2H), 2.38 (s, 3H), 2.05-1.93 (m, 2H), 1.54 (d, J=6.6 Hz, 3H), 1.24 (s, 1H).

Aufarbeitung

  1. customwere separated
  2. extractionthe water phase was extracted with DCM (3×), organic phases
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified
  7. washeluting with MeOH (including 3% NH3, 4-5%) in DCM

Quellen und Nachweise

ORD-Eintrag
ord-16dd6213d75b46b281cb5f4cac3b1daf
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09266883B2

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