2-hydroxy-N,N-dimethyl-2-{5-[3-oxazol-2-yl-1(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide → 2-hydroxy-N,N-dimethyl-2-{5-[3-oxazol-2-yl-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide

HRID 886636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 886636
[OH:1][CH:2]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[O:24][CH:25]=[CH:26][N:27]=4)=[CH:21][N:20](COCC[Si](C)(C)C)[C:17]3=[N:18][CH:19]=2)[CH:13]=1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4]>ClCCl.FC(F)(F)C([O-])=O>[OH:1][CH:2]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[O:24][CH:25]=[CH:26][N:27]=4)=[CH:21][NH:20][C:17]3=[N:18][CH:19]=2)[CH:13]=1)[C:3]([N:5]([CH3:6])[CH3:7])=[O:4]

Komponenten

3

Edukt 1

HCID 598250292-hydroxy-N,N-dimethyl-2-{5-[3-oxazol-2-yl-1(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide

Produkt 1

HCID 598248372-hydroxy-N,N-dimethyl-2-{5-[3-oxazol-2-yl-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamideAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22481192Dichloromethane trifluoroacetateLösungsmittel

Versuchsvorschrift

2-Hydroxy-N,N-dimethyl-2-{5-[3-oxazol-2-yl-1(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide (10 mg, 0.02 mmol) was stirred in dichloromethane/trifluoroacetate acid (1 ml/1 ml) at room temperature for 2 hours. The solvents were removed under vacuum and the crude was stirred in dichloromethane/ethylenediamine (1 ml/1 ml) for 2 hours at room temperature. Again the solvents was removed under vacuum and the crude was dissolved in DMSO, filtered and purified by reverse phase HPLC, lyophilized afforded 2-hydroxy-N,N-dimethyl-2-{5-[3-oxazol-2-yl-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetamide (2 mg, 31% yield). 1H NMR (500 MHz, DMSO-d6) δ 2.81 (s, 3H), 2.96 (s, 3H), 5.58 (s, 1H), 6.22 (s, 1H), 7.28 (s, 1H), 8.04 (t, 1H), 8.76 (s, 1H), 8.22 (s, 1H), 8.52 (d, 1H), 8.62 (s, 2H0, 8.83 (d, 1H). MS: m/z 364.0 (M+H+).

Aufarbeitung

  1. customThe solvents were removed under vacuum
  2. customAgain the solvents was removed under vacuum
  3. dissolutionthe crude was dissolved in DMSO
  4. filtrationfiltered
  5. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-18971711016f4322bceddc1ebf743754
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242280B2

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