Triethylamine → Methanesulfonic acid 5-[(5-bromo-imidazo[1,2-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]-2-morpholin-4-yl-benzyl ester

HRID 1921851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921851
[C:1]([O:5][C:6](=[O:32])[N:7]([C:22]1[C:23]2[N:24]([CH:29]=[CH:30][N:31]=2)[C:25]([Br:28])=[CH:26][N:27]=1)[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:10]([CH2:20][OH:21])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl.C(OCC)(=O)C>[Br:28][C:25]1[N:24]2[CH:29]=[CH:30][N:31]=[C:23]2[C:22]([N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:32])[C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[C:10]([CH:9]=2)[CH2:20][O:21][S:41]([CH3:40])(=[O:43])=[O:42])=[N:27][CH:26]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86652629(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-hydroxymethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 86652630Methanesulfonic acid 5-[(5-bromo-imidazo[1,2-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]-2-morpholin-4-yl-benzyl esterAusbeute 113,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled solution (0° C.) of (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-hydroxymethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester (0.17 g, 0.34 mmol) in DCM (0.5 mL), is added triethylamine (0.104 mL, 0.74 mmol) followed by methanesulfonyl chloride (0.046 mL, 0.6 mmol). The reaction mixture is stirred at 0° C. for 1 hour and an additional hour at room temperature. The reaction mixture is diluted with ethyl acetate and washed with water. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to give the title compound (0.224 g) used in the next step without further purification.

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c2f68fd1150b442497a3b75cf619f4c7
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173656B2

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