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Formaldehyde → 5-chloro-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-3-(methyl(1-methylpiperidin-4-yl)amino)benzamide

HRID 2208726
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2208726
[Cl:1][C:2]1[CH:3]=[C:4]([N:22]([CH3:29])[CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[C:5]([CH3:21])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][C:11]1[C:12](=[O:19])[NH:13][C:14]([CH3:18])=[CH:15][C:16]=1[CH3:17])=[O:8].C=O.[C:32]([BH3-])#N.[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([N:22]([CH3:29])[CH:23]2[CH2:28][CH2:27][N:26]([CH3:32])[CH2:25][CH2:24]2)[C:5]([CH3:21])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][C:11]1[C:12](=[O:19])[NH:13][C:14]([CH3:18])=[CH:15][C:16]=1[CH3:17])=[O:8]
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Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66575836HCID 66575836, Verbindung

Produkt 1

HCID 708740405-chloro-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-3-(methyl(1-methylpiperidin-4-yl)amino)benzamideAusbeute 24,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5-Chloro-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-3-(methyl(piperidin-4-yl)amino)benzamide (0.08 g, 0.192 mmol) was dissolved in methanol (5 mL) and cooled to 0° C., formalin (0.028 g, 0.965 mmol) was added. Resulting reaction mass was stirred at same temperature for 30 minutes. Sodium cyanoborohydride (0.023 g, 0.38 mmol) was added to above reaction mass and stirred at room temperature for 4 h. After completion, solvent were removed under reduced pressure and water was added to the residue, extraction was carried out using DCM. Combined organic layers were dried, concentrated and purified by column chromatography giving the desired compound (0.02 g, 24%): LCMS: 431.25 (M+1)+; HPLC: 98.80% (@ 254 nm) (Rt; 4.757; Method: Column: YMC ODS-A 150 mm×4.6 mm×5μ; Mobile Phase: A; 0.05% TFA in water/B; 0.05% TFA in acetonitrile; Inj. Vol: 10 μL, Col. Temp.: 30° C.; Flow rate: 1.4 mL/min.; Gradient: 5% B to 95% B in 8 min, Hold for 1.5 min, 9.51-12 min 5% B); 1H NMR (DMSO-d6, 400 MHz) δ 11.46 (s, 1H), 8.20 (t, 1H), 7.15 (d, 1H, J=1.2 Hz), 6.94 (d, 1H, J=2 Hz), 5.85 (s, 1H), 4.25 (d, 2H, J=4.8 Hz), 3.05 (bs, 2H), 2.88 (bs, 1H), 2.55 (s, 3H), 2.44 (bs, 2H), 2.18 (s, 3H), 2.14 (s, 3H), 2.10 (s, 3H), 1.68 (bs, 4H).

Aufarbeitung

  1. customResulting
  2. customreaction mass
  3. stirringstirred at room temperature for 4 h
  4. customAfter completion, solvent were removed under reduced pressure and water
  5. additionwas added to the residue, extraction
  6. customCombined organic layers were dried
  7. concentrationconcentrated
  8. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b494263e9d32489e96781198da5e47c1
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09376422B2

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