Methylamine → 2,6-Diisopropyl-3-methylaminomethyl-4-(4-fluorophenyl)-5-pentyl-pyridine

HRID 324834

Reaktionsgleichung

Reaktionsgleichung von HRID 324834
[Cl-].C[NH3+].CN.[C:6]([BH3-])#[N:7].[Na+].[CH:10]([C:13]1[C:18]([CH:19]=O)=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:16]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:15]([CH:33]([CH3:35])[CH3:34])[N:14]=1)([CH3:12])[CH3:11]>CO>[CH:10]([C:13]1[C:18]([CH2:19][NH:7][CH3:6])=[C:17]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)[C:16]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:15]([CH:33]([CH3:34])[CH3:35])[N:14]=1)([CH3:11])[CH3:12]

Komponenten

6

Edukt 4

HCID 6329MethylamineHCID 11637Methanamine, hydrochloride (1:1)HCID 5003444Sodium cyanoborohydrideHCID 220049662,6-Diisopropyl-4-(4-fluorophenyl)-5-pentyl-3-pyridine-carboxaldehyde

Produkt 1

HCID 220051962,6-Diisopropyl-3-methylaminomethyl-4-(4-fluorophenyl)-5-pentyl-pyridineAusbeute 33,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

Methylammonium chloride (37.99 mg, 0.563 mmol) was added to a stirred solution of methylamine in methanol (2M, 0.28 mL) under argon in an oven-dried round bottom flask equipped with a stir bar. Then sodium cyanoborohydride (4 eq., 10.60 mg, 0.169 mmol) was added and 2,6-diisopropyl-4-(4-fluorophenyl)-5-pentyl-3-pyridinecarboxaldehyde (Example 114, Step A) (100 mg, 0.281 mmol) was added as a solution in methanol (2 mL). The reaction was refluxed for 18 hours and then quenched with water. Concentration and addition of CH2Cl2 (25 mL) allowed washings with water (2×15 mL), brine (1×25 mL), following which the solution was dried with MgSO4, filtered, and concentrated to afford a clear oil. Flash chromatography using silica gel (40% ether/CH2Cl2) yielded the title compound as a white solid (21 mg, 0.057 mmol, 20%). 1H NMR (300 MHz, CDCl3): δ 7.13 (m, 4 H), 3.26 (m, 4 H), 2.24 (m, 5 H), 1.20 (m, 19 H), 0.783 (t, J=6.6 Hz, 3 H). FAB-MS: calcd for (C24H35FN2) 370, found 371 (M+H). mp 77-79° C. Rf=0.2 (20% ether/CH2Cl2).

Aufarbeitung

  1. customequipped with a stir bar
  2. temperatureThe reaction was refluxed for 18 hours
  3. customquenched with water
  4. concentrationConcentration and addition of CH2Cl2 (25 mL)
  5. washwashings with water (2×15 mL), brine (1×25 mL)
  6. dry with materialwas dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a clear oil

Quellen und Nachweise

ORD-Eintrag
ord-a66e4940a0384cd190656948c1188590
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218431B1

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