1-Hydroxybenzotriazole → 5-Bromoisoquinolin-4-carboxylic amide

HRID 1470484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470484
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:12]([OH:14])=O)=[CH:5][N:6]=[CH:7]2.CC[N:17](C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:12]([NH2:17])=[O:14])=[CH:5][N:6]=[CH:7]2

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 682819235-Bromoisoquinoline-4-carboxylic acid

Produkt 1

HCID 682818895-Bromoisoquinolin-4-carboxylic amideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-bromoisoquinoline-4-carboxylic acid (Intermediate-17) (1 equiv, 2.0 mmol) in dry THF (10.0 ml) were added, DIPEA (3 equiv), HOBT (1.5 equiv), EDC.HCl (1.5 equiv) at RT and the mixture was stirred for 10 min. To this, corresponding amine (1.2 equiv) was added and the reaction mixture was stirred overnight. After completion (TLC), it was concentrated under reduced pressure and the crude product was purified by flash column chromatography to furnish the corresponding amide derivative (60-80%).

Aufarbeitung

  1. concentrationAfter completion (TLC), it was concentrated under reduced pressure
  2. customthe crude product was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d7796424a0f54b34821a4182919c440e
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006442B2

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