Triethylamine → 4-[(3-Aminoisoquinolin-1-yl)ethynyl]benzoyl-2(S)-phenylsulfonylamino-beta-alanine ethyl ester

HRID 583712

Reaktionsgleichung

[CH2:1]([O:3][C:4](=[O:28])[C@@H:5]([NH:18][S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])[CH2:6][NH:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([C:15]#[CH:16])=[CH:11][CH:10]=1)[CH3:2].[NH2:29][C:30]1[N:31]=[C:32](Br)[C:33]2[C:38]([CH:39]=1)=[CH:37][CH:36]=[CH:35][CH:34]=2.C(N(CC)CC)C>C(#N)C.CCOC(C)=O.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:28])[C@@H:5]([NH:18][S:19]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)(=[O:20])=[O:21])[CH2:6][NH:7][C:8](=[O:17])[C:9]1[CH:10]=[CH:11][C:12]([C:15]#[C:16][C:32]2[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:39]=[C:30]([NH2:29])[N:31]=2)=[CH:13][CH:14]=1)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Ethyl ester 35-3 (0.50 g, 1.25 mmol), 3-amino-1-bromoisoquinoline (0.279 g, 1.25 mmol), triethylamine (0.697 mL, 5.00 mmol), CuI (10 mg, 0.053 mmol), and (Ph3P)2PdCl2 (20 mg, 0.028 mmol) were combined in 5 mL acetonitrile in a sealed pressure tube under Ar and heated to 100° C. overnight. The dark solution was cooled and diluted with EtOAc, then washed with water (2×) and brine, dried (MgSO4), filtered, and concentrated. Flash chromatography (silica, 75% EtOAc/Hexane) gave 35-4 as a greenish foam.

Aufarbeitung

temperatureThe dark solution was cooled
washwashed with water (2×) and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-6898179a3d1c4f5ea3eb85a2fc633743
Quelldatensatz: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05929120

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