Trifluoroacetic acid → N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 522987

Reaktionsgleichung

Reaktionsgleichung von HRID 522987
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([N:17]([CH3:24])[C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[N:15]=2)[N:10](COCC[Si](C)(C)C)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([N:17]([CH3:24])[C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 90041212N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Produkt 1

HCID 73295951N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (38 mg, 83.6 μmol) was dissolved in dichloromethane (1.5 mL) and treated with trifluoroacetic acid (191 mg, 129 μL, 1.67 mmol). After 16 h, the mixture was concentrated and the residue re-dissolved in dichloromethane (1.5 mL), methanol (0.75 mL) and ammonium hydroxide (0.2 mL) and the mixture stirred at room temperature for 1 h. The mixture was concentrated then triturated with water and filtered to obtain a solid. This was washed with ether then dried to give N-tert-butyl-2-(methyl(pyridin-3-yl)amino)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (16 mg, 49.3 μmol, 59%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d) δ ppm: 12.33 (s, 1H), 8.64 (d, J=2.5, 1 H), 8.40 (dd, J=4.7, 1.2, 1 H), 8.05 (d, J=3.1, 1 H), 7.96 (s, 1H), 7.92 (s, 1H), 7.82 (m, 1H), 7.46 (m, 1H), 3.50 (s, 3H), 1.32 (s, 9H); MS (EI/CI) m/z: 325.1 [M+H].

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue re-dissolved in dichloromethane (1.5 mL)
  3. concentrationThe mixture was concentrated
  4. customthen triturated with water
  5. filtrationfiltered
  6. customto obtain a solid
  7. washThis was washed with ether
  8. customthen dried

Quellen und Nachweise

ORD-Eintrag
ord-30a7237b828a4d21aef5c77f1fb6d6cb
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09334278B2

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