Diisopropylethylamine → Ethyl(+/-)-4-(1-((3-methylquinolin-2-yl)amino)butyl)benzoate

HRID 2281116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2281116
[NH2:1][CH:2]([C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].[CH3:17][C:18]1[CH:19]=[N+:20]([O-])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>C([O-])(O)=O.[Na+].ClCCl>[CH3:17][C:18]1[C:19]([NH:1][CH:2]([C:6]2[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=2)[CH2:3][CH2:4][CH3:5])=[N:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 70214663-Methylquinoline N-oxide2×HCID 71243833Ethyl(+/-)-4-(1-aminobutyl)benzoate

Produkt 1

HCID 71243834Ethyl(+/-)-4-(1-((3-methylquinolin-2-yl)amino)butyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Intermediate 2 (22.9 g, 104 mmol) was combined with 3-methylquinoline-N-oxide (Intermediate 3, 17.3 g, 109 mmol) and dichloromethane (414 mL). Diisopropylethylamine (68.0 mL, 389 mmol) was added, followed by bromotripyrrolidinophosphonium hexafluorophosphate (61.0 g, 130 mmol). The solution was stirred at room temperature for 12 h before diluting with sat. aq NaHCO3 (400 mL). The mixture was extracted with ethyl acetate (3×400 mL). The combined organics were dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure. Purification by silica gel flash chromatography (ethyl acetate/heptane) gave ethyl (+/−)-4-(1-((3-methylquinolin-2-yl)amino)butyl)benzoate (Intermediate 4). 1H NMR (400 MHz, CDCl3) δ 7.99 (d, J=8.2 Hz, 2 H), 7.65-7.58 (m, 2 H), 7.56-7.48 (m, 3 H), 7.43 (t, J=7.5 Hz, 1 H), 7.16 (t, J=7.4 Hz, 1 H), 5.50 (q, J=7.2 Hz, 1 H), 4.79 (d, J=7.0 Hz, 1 H), 4.35 (q, J=7.0 Hz, 2 H), 2.30 (s, 3 H), 2.04-1.83 (m, 2 H), 1.54-1.39 (m, 2 H), 1.37 (t, J=7.1 Hz, 3 H), 0.98 (t, J=7.4 Hz, 3 H).

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate (3×400 mL)
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customPurification by silica gel flash chromatography (ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-e36b0740e0104d0e8f14fb310379cb02
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139538B2

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