Triethylamine → (S)-N-(1-(8-chloro-1-(2-morpholinoethyl)isoquinolin-3-yl)ethyl)thiazolo[5,4-d]pyrimidin-7-amine

HRID 1396621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1396621
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[N:9][C:8]([C@@H:20]([NH2:22])[CH3:21])=[CH:7]2.Cl[C:24]1[C:25]2[N:32]=[CH:31][S:30][C:26]=2[N:27]=[CH:28][N:29]=1.C(N(CC)CC)C>CCCCO>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[N:9][C:8]([C@@H:20]([NH:22][C:24]1[C:25]3[N:32]=[CH:31][S:30][C:26]=3[N:27]=[CH:28][N:29]=1)[CH3:21])=[CH:7]2

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2630077-Chlorothiazolo[5,4-D]pyrimidineHCID 68747373(S)-1-(8-chloro-1-(2-morpholinoethyl)isoquinolin-3-yl)ethanamine

Produkt 1

HCID 57330000(S)-N-(1-(8-chloro-1-(2-morpholinoethyl)isoquinolin-3-yl)ethyl)thiazolo[5,4-d]pyrimidin-7-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of (S)-1-(8-chloro-1-(2-morpholinoethyl)isoquinolin-3-yl)ethanamine 71 (100 mg, 0.31 mmol, 1 eq), 7-chlorothiazolo[5,4-d]pyrimidine (E-4) (108 mg, 0.63 mmol, 2 eq) and triethylamine (130 mg, 1.25 mmol, 4.0 eq) in n-BuOH (40 mL) was stirred at reflux for 16 h. The reaction mixture was cooled to RT and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (1-5% MeOH-DCM) to afford the product (S)—N-(1-(8-chloro-1-(2-morpholinoethyl)isoquinolin-3-yl)ethyl)thiazolo[5,4-d]pyrimidin-7-amine 72. ESI-MS m/z: 455.0 [M+H]+.

Aufarbeitung

  1. temperatureat reflux for 16 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel (1-5% MeOH-DCM)

Quellen und Nachweise

ORD-Eintrag
ord-90b4a6da34e944ff9f175dbadc674060
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901133B2

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