1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52950745, Verbindung

HRID 2172098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2172098
Cl.[CH3:2]/[C:3](=[CH:10]\[CH3:11])/[CH2:4][O:5][CH:6]1[CH2:9][NH:8][CH2:7]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.Cl.[O:43]=[C:44]1[NH:53][C:52]2[N:51]=[CH:50][C:49](/[CH:54]=[CH:55]/[C:56](O)=[O:57])=[CH:48][C:47]=2[CH2:46][CH2:45]1>CN(C)C=O.O.C(OCC)(=O)C>[CH3:2]/[C:3](=[CH:10]\[CH3:11])/[CH2:4][O:5][CH:6]1[CH2:9][N:8]([C:56](=[O:57])/[CH:55]=[CH:54]/[C:49]2[CH:48]=[C:47]3[C:52](=[N:51][CH:50]=2)[NH:53][C:44](=[O:43])[CH2:45][CH2:46]3)[CH2:7]1

Komponenten

9

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid HydrochlorideHCID 86672985(E)-3-(2-Methylbut-2-enyloxy)azetidine hydrochloride

Produkt 1

HCID 52950745HCID 52950745, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(E)-3-(2-Methylbut-2-enyloxy)azetidine hydrochloride (168 mg, 0.94 mmol), EDCI (182 mg, 0.94 mmol), HOBt (132 mg, 0.94 mmol) and diisopropylethylamine (276 μL, 1.58 mmol) were successively added to a solution of (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)-acrylic acid hydrochloride (161 mg, 0.63 mmol) in dimethylformamide (12 mL) at room temperature. The reaction mixture was stirred overnight then diluted by addition of ethyl acetate (40 mL) and water (40 mL). The aqueous layer was separated and extracted with ethyl acetate (2×40 mL). The combined organic phases were washed with a saturated solution of sodium chloride (3×50 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel using dichloromethane/methanol (98:2) as eluent. After trituration in diethyl ether, petroleum ether and methanol, the title product was obtained as a white solid (46 mg, 21%).

Aufarbeitung

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (2×40 mL)
  3. washThe combined organic phases were washed with a saturated solution of sodium chloride (3×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9a48ecc467a04ec1af2c04819d4162e5
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051321B2

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