Diisopropylethylamine → Tert-butyl 2-(2-(4-(3-azidopropylamino)-6-(2-hydroxyethylamino)-1,3,5-triazin-2-ylamino)ethoxy)ethylcarbamate

HRID 1404417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1404417
CC[N:3](C(C)C)C(C)C.NCCO[CH2:14][CH2:15][O:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].[N:27]([CH2:30][CH2:31][CH2:32][NH:33][C:34]1[N:39]=[C:38](Cl)[N:37]=[C:36]([NH:41][CH2:42][CH2:43][OH:44])[N:35]=1)=[N+:28]=[N-:29]>C1COCC1>[N:27]([CH2:30][CH2:31][CH2:32][NH:33][C:34]1[N:35]=[C:36]([NH:41][CH2:42][CH2:43][OH:44])[N:37]=[C:38]([NH:3][CH2:14][CH2:15][O:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[N:39]=1)=[N+:28]=[N-:29]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 9881394tert-butyl N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamateHCID 866721782-(4-(3-Azidopropylamino)-6-chloro-1,3,5-triazin-2-ylamino)ethanol

Produkt 1

HCID 86672180Tert-butyl 2-(2-(4-(3-azidopropylamino)-6-(2-hydroxyethylamino)-1,3,5-triazin-2-ylamino)ethoxy)ethylcarbamateAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

DIPEA (142 mg, 1.10 mmol), tert-butyl 2-(2-(2-aminoethoxy)ethoxy)ethylcarbamate (273 mg, 1.10 mmol), and 2 (150 mg, 0.55 mmol) were dissolved in THF (5 mL). The mixture was stirred at 70° C. under N2 overnight. The solvent was removed under reduced pressure. The resulting residue was purified by column chromatography on silica gel (eluent CH3OH/CH2Cl2=2/98) to give 3 as a white solid (124 mg, 47%): ESI-MS m/z 485.2 (M+H+) calculated for C19H37N10O5 485.3.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customThe resulting residue was purified by column chromatography on silica gel (eluent CH3OH/CH2Cl2=2/98)

Quellen und Nachweise

ORD-Eintrag
ord-0f7cfccab33445ac85b318cebb04b4b6
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912323B2

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