Dimethylamine → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-dimethylaminomethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

HRID 1925002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1925002
[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([N:11]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:12]2[CH:13]=[CH:14][C:15]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[C:16]([CH:23]=2)[CH2:17]OS(C)(=O)=O)=[N:4][CH:3]=1.[CH3:37][NH:38][CH3:39].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[NH3:4].[C:33]([O:32][C:30](=[O:31])[N:11]([C:5]1[C:6]2[N:7]([CH:8]=[CH:9][N:10]=2)[C:2]([Br:1])=[CH:3][N:4]=1)[C:12]1[CH:13]=[CH:14][C:15]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)=[C:16]([CH2:17][N:38]([CH3:39])[CH3:37])[CH:23]=1)([CH3:35])([CH3:34])[CH3:36]

Komponenten

6

Edukt 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 86652630Methanesulfonic acid 5-[(5-bromo-imidazo[1,2-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]-2-morpholin-4-yl-benzyl ester

Produkt 2

HCID 222AmmoniaHCID 86652631(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-dimethylaminomethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl esterAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of methanesulfonic acid 5-[(5-bromo-imidazo[1,2-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]-2-morpholin-4-yl-benzyl ester (0.098 g, 0.169 mmol) in THF (0.5 mL) is added 2M N,N-dimethylamine solution in THF (0.50 mL, 1.1 mmol) followed by K2CO3 (0.028 g, 0.202 mmol). The reaction mixture is stirred at room temperature for 1.5 hours and at 75° C. for an additional 3 hours. The solvent is removed under vacuum and the residue is partitioned between ethyl acetate and water. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to give the crude compound which is purified by silica gel column chromatography. Elution using 97:3 DCM:NH3 (7M in MeOH) affords the title compound (0.0543 g, 61%). LCMS: Rt 2.37 min (95%), m/z (ES+) 531/533 (M+H)+.

Aufarbeitung

  1. customThe solvent is removed under vacuum
  2. customthe residue is partitioned between ethyl acetate and water
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude compound which
  7. customis purified by silica gel column chromatography
  8. washElution

Quellen und Nachweise

ORD-Eintrag
ord-c725af116c1c4a06b43680fa4cb3b4fb
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178530B2

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