1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 52950524, Verbindung

HRID 2172004Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2172004
Cl.[O:2]=[C:3]1[NH:12][C:11]2[N:10]=[CH:9][C:8](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)=[CH:7][C:6]=2[CH2:5][CH2:4]1.F[C:19](F)(F)C(O)=O.[NH:25]1[CH2:29][CH2:28][CH2:27][C@@H:26]1[C:30]1[O:31][C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[O:31]1[C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=[C:30]1[CH:26]1[CH2:19][CH2:27][CH2:28][CH2:29][N:25]1[C:15](=[O:17])/[CH:14]=[CH:13]/[C:8]1[CH:7]=[C:6]2[C:11](=[N:10][CH:9]=1)[NH:12][C:3](=[O:2])[CH2:4][CH2:5]2

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid HydrochlorideHCID 709267682-[(2R)-Pyrrolidin-2-yl]-1,3-benzoxazole trifluoroacetate

Produkt 1

HCID 52950524HCID 52950524, VerbindungAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 16 mL vial flask was successively charged with (2E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride (60 mg, 0.24 mmol), DMF (5.8 mL), 2-[(2R)-pyrrolidin-2-yl]-1,3-benzoxazole trifluoroacetate (0.31 mmol theory; which may be prepared as described in Step 3), DIPEA (96 μL, 0.58 mmol), DMAP (2.4 mg, 0.02 mmol) and EDAC (56 mg, 0.29 mmol). The reaction mixture was stirred at room temperature overnight and concentrated to dryness. The residue was purified on preparative TLC (eluent: dichloromethane/MeOH, 95/5) and column chromatography (eluent: dichloromethane/MeOH, 98/2) to give the title compound (12 mg, 13%) as a white solid.

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. customThe residue was purified on preparative TLC (eluent: dichloromethane/MeOH, 95/5) and column chromatography (eluent: dichloromethane/MeOH, 98/2)

Quellen und Nachweise

ORD-Eintrag
ord-3419011c54484b5291229ce96fb983b0
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051321B2

Notizen zur Reaktion

Wird geladen…