1-Benzyloxycarbonyl-2-(1-aminoethyl)-4-tert-butyloxycarbonylpiperazine → HCID 70123251, Verbindung

HRID 429287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 429287
Cl[C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[CH:9]2)[C:5]([Br:17])=[CH:4][N:3]=1.[CH2:18]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH:29]1[CH:41]([NH2:43])[CH3:42])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH2:18]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:30][CH:29]1[CH:41]([NH:43][C:2]1[N:7]=[C:6]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[CH:9]2)[C:5]([Br:17])=[CH:4][N:3]=1)[CH3:42])=[O:27])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

6

Edukt 2

HCID 183428831-Benzyloxycarbonyl-2-(1-aminoethyl)-4-tert-butyloxycarbonylpiperazineHCID 22731922HCID 22731922, Verbindung

Produkt 1

HCID 70123251HCID 70123251, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-4-(benzimidazol-1-yl)-5-bromopyrimidine (100 mg) and 1-benzyloxycarbonyl-2-(1-aminoethyl)-4-tert-butyloxycarbonylpiperazine, diastereomer 1 (EXAMPLE 14 Step D; 115 mg), in 10 mL of toluene was heated to 100° C. and stirred overnight (14 h) at this temperature. The mixture was then cooled and diluted with 20 mL of EtOAc and 30 mL of water. The phases were separated and the aqueous phase was extracted with 2×20 mL of EtOAc. The combined organics were dried over MgSO4 and concentrated. The residue was purified by flash chromatography, eluting with 20:1 hexanes-acetone to provide 133 mg of the title compound. Mass spectrum (ESI) 638.4 (M+1).

Aufarbeitung

  1. temperatureThe mixture was then cooled
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with 2×20 mL of EtOAc
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 20:1 hexanes-acetone

Quellen und Nachweise

ORD-Eintrag
ord-218e18bef09e40be99eff1991c35638c
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316444B1

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