Isoquinoline-1-carboxylic acid → Ethyl (3-bromo-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetate

HRID 1372719

Reaktionsgleichung

Reaktionsgleichung von HRID 1372719
[C:1]1([C:11]([OH:13])=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][C:16]=1[Br:27].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[Br:27][C:16]1[CH:17]=[C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:19]=[CH:20][C:15]=1[NH:14][C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1)=[O:13]

Komponenten

8

Edukt 4

HCID 68092Isoquinoline-1-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19702145Ethyl 2-(4-amino-3-bromophenyl)acetate

Produkt 1

HCID 58778618Ethyl (3-bromo-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetateAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In DMF (15 ml) were dissolved 1-isoquinolinecarboxylic acid (1.00 g, 5.77 mmol), ethyl 4-amino-3-bromophenylacetate (1.49 g, 5.77 mmol), HOBt (0.39 g, 2.89 mmol), and DMAP (0.14 g, 1.15 mmol). To the resulting solution was added EDC HCl (1.33 g, 6.93 mmol). After stirring at 60° C. for 5 hours, the reaction mixture was cooled to room temperature. Water was added, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane:ethyl acetate (4:1, v/v) eluate fractions, ethyl (3-bromo-4-((1-isoquinolinylcarbonyl)amino)phenyl)acetate (1.64 g, 69%) was obtained as a yellow solid.

Aufarbeitung

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane:ethyl acetate (4:1

Quellen und Nachweise

ORD-Eintrag
ord-4f6477460f244b1295b64770b1c2e833
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157487B2

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