Ethylenediamine → 2-Hydroxy-1,1-dimethyl-ethyl-amide

HRID 246561

Reaktionsgleichung

Reaktionsgleichung von HRID 246561
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([NH:23][C:24]([CH3:28])([CH3:27])[CH2:25][OH:26])=[O:22])=[CH:19][N:18](COCC[Si](C)(C)C)[C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.FC(F)(F)C(O)=[O:40].C(N)CN>ClCCl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([OH:40])=[O:22])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[OH:26][CH2:25][C:24]([NH-:23])([CH3:28])[CH3:27]

Komponenten

6

Edukt 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 712804242-(6-Fluoro-1-methyl-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Produkt 2

HCID 712796392-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 866779892-Hydroxy-1,1-dimethyl-ethyl-amideAusbeute 174,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2-(6-Fluoro-1-methyl-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.08 g, 0.156 mmol), and trifluoroacetic acid (1 mL, 13.0 mmol) were stirred in dichloromethane for 15 h. The reaction mixture was concentrated in vacuo then ethylenediamine (1 mL, 14.8 mmol) in dichloromethane (5 mL) was added. After 1 h, the mixture was concentrated to dryness and water (1 mL) added. The solid precipitate was collected by filtration and dried to give 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl-amide (24 mg, 36%). MS (M+H)+=383; 1H NMR (DMSO-d6) δ: 9.07 (s, 1H), 8.60 (dd, J=8.7, 5.5 Hz, 1H), 8.37 (s, 1H), 7.91 (s, 1H), 7.66 (d, J=9.8 Hz, 1H), 7.15 (t, J=8.3 Hz, 1H), 4.14 (s, 3H), 3.62 (s, 2H), 1.45 (s, 6H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. concentrationthe mixture was concentrated to dryness and water (1 mL)
  3. additionadded
  4. filtrationThe solid precipitate was collected by filtration
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7cd1dc268fce4e0eb78b95b2101fbd68
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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