1,2-Dichloroethane → 2-(4-isopropylphenyl)-N-[(1R)-1-(5-methoxypyridin-2-yl)ethyl]acetamide

HRID 2383526

Reaktionsgleichung

Reaktionsgleichung von HRID 2383526
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl.[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([C@H:23]([NH2:25])[CH3:24])=[N:21][CH:22]=1.C(Cl)CCl.ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([NH:25][C@@H:23]([C:20]2[CH:19]=[CH:18][C:17]([O:16][CH3:15])=[CH:22][N:21]=2)[CH3:24])=[O:13])=[CH:8][CH:9]=1)([CH3:2])[CH3:3]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 782304-Isopropylphenylacetic acidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 66892986(R)-1-(5-Methoxypyridin-2-yl)ethanamine hydrochloride

Produkt 1

HCID 247654842-(4-isopropylphenyl)-N-[(1R)-1-(5-methoxypyridin-2-yl)ethyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 4-isopropylphenylacetic acid (2.5 g, 14.0 mmol), (1R)-1-(5-methoxypyridin-2-yl)ethylamine hydrochloride (3.2 g, 16.8 mmol), EDC (3.24 g, 16.9 mmol), and 1-hydroxy-7-azabenzotriazole (2.3 g, 16.8 mmol) in DMF (60 mL) was added N,N-diisopropylethylamine (5.2 mL, 29.6 mmol). The reaction mixture was stirred at room temperature for 2.5 h and then concentrated to 20 mL and diluted with CH2Cl2 (100 mL). The solution was washed with water (100 mL) and the aqueous layer was extracted with CH2Cl2 (2×75 mL). The combined organic layer was washed with water (100 mL), dried over MgSO4, concentrated and purified by normal phase chromatography (10-100% EtOAc/Hexanes) to give of 2-(4-isopropylphenyl)-N-[(1R)-1-(5-methoxypyridin-2-yl)ethyl]acetamide as a pale yellow solid. 1H NMR (CDCl3, 400 MHz) δ 8.14 (d, J=2.56 Hz, 1H), 7.20 (m, 4H), 7.13 (m, 2H), 6.69 (d, J=6.78 Hz, 1H), 5.08 (quint., J=6.96 Hz, 1H), 3.84 (s, 3H), 3.55 (s, 2H), 2.90 (sept., J=6.96 Hz, 1H), 1.39 (d, J=6.77 Hz, 3H), 1.25 (d, J=6.96 Hz, 6H); MS (Electrospray): m/z 313.4 (M+H).

Aufarbeitung

  1. concentrationconcentrated to 20 mL
  2. additiondiluted with CH2Cl2 (100 mL)
  3. washThe solution was washed with water (100 mL)
  4. extractionthe aqueous layer was extracted with CH2Cl2 (2×75 mL)
  5. washThe combined organic layer was washed with water (100 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custompurified by normal phase chromatography (10-100% EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-cca774c1b827482dbcd94ff4b6cd4da1
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263627B2

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