Diisopropylethylamine → 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide

HRID 1799119

Reaktionsgleichung

Reaktionsgleichung von HRID 1799119
C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.[O:34]1[CH2:38][CH2:37][O:36][CH:35]1[CH2:39][CH2:40][C:41]1[S:45][C:44]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[N:43][C:42]=1[C:52]([OH:54])=O.CCN(C(C)C)C(C)C.[N:64]1[C:72]2[C:67](=[N:68][CH:69]=[CH:70][CH:71]=2)[S:66][C:65]=1[C:73]1[CH:79]=[CH:78][CH:77]=[CH:76][C:74]=1[NH2:75].C([O-])(O)=O.[Na+]>CN(C=O)C>[O:36]1[CH2:37][CH2:38][O:34][CH:35]1[CH2:39][CH2:40][C:41]1[S:45][C:44]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[N:43][C:42]=1[C:52]([NH:75][C:74]1[CH:76]=[CH:77][CH:78]=[CH:79][C:73]=1[C:65]1[S:66][C:67]2[C:72]([N:64]=1)=[CH:71][CH:70]=[CH:69][N:68]=2)=[O:54]

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 581014682-(Thiazolo[5,4-b]pyridin-2-yl)anilineHCID 585519085-(2-(1,3-Dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acidHCID 866211442-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate Methanaminium

Produkt 1

HCID 585519015-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamideAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU) (669 mg, 1.8 mmol) was added to a solution of 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acid (504 mg, 1.7 mmol), DIPEA (613 μL, 3.5 mmol), and 2-(thiazolo[5,4-b]pyridin-2-yl)aniline b(250 mg, 1.1 mmol) in DMF (7 mL). The reaction mixture was stirred for 16 h, poured into sat aq NaHCO3 and extracted with EtOAc. The organic fractions were washed with brine, dried and concentrated. The crude product was crystallized from EtOH to give 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide (372 mg, 66% yield).

Aufarbeitung

  1. additionpoured
  2. extractionextracted with EtOAc
  3. washThe organic fractions were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was crystallized from EtOH

Quellen und Nachweise

ORD-Eintrag
ord-daf8f2ab3a134fd9b0af9d92f9cc8dce
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343997B2

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