Triethylamine → (E)-3-(4-{(S)-1-[2-(2-methyl-1H-indol-3-yl)-acetyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester

HRID 549388Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 549388
Cl.[CH3:2][O:3][C:4](=[O:18])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[CH:9][CH:8]=1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH3:48][C:49]1[NH:50][C:51]2[C:56]([C:57]=1[CH2:58][C:59](O)=[O:60])=[CH:55][CH:54]=[CH:53][CH:52]=2>CN(C)C=O.ClCCl>[CH3:2][O:3][C:4](=[O:18])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:59](=[O:60])[CH2:58][C:57]2[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[NH:50][C:49]=2[CH3:48])=[CH:9][CH:8]=1

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 5891072-Methyl-1H-indole-3-acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67158659(E)-3-((S)-4-pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester hydrochloride

Produkt 1

HCID 67158759(E)-3-(4-{(S)-1-[2-(2-methyl-1H-indol-3-yl)-acetyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl esterAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of (E)-3-((S)-4-pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester hydrochloride (0.3 g, 1.12 mmol) in N,N-dimethylformamide (20 mL) was added sequentially triethylamine (0.5 mL, 3.58 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.24 g, 1.25 mmol), 1-hydroxybenzotriazole (0.17 g, 1.25 mmol) and 2-methylindole-3-acetic acid (0.235 g, 1.24 mmol). The reaction was stirred for 16 h and diluted with dichloromethane, and the solution was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (2% methanol in dichloromethane) to obtain (E)-3-(4-{(S)-1-[2-(2-methyl-1H-indol-3-yl)-acetyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester as a colorless oil (0.42 g, 1.03 mmol, 93% yield).

Aufarbeitung

  1. washthe solution was washed with a saturated aqueous solution of sodium chloride
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel column chromatography (2% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-0642422c118645aab201558a931166fe
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943652B2

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