Trifluoroacetic acid → 2-(6-methoxy-indazol-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

HRID 246501

Reaktionsgleichung

Reaktionsgleichung von HRID 246501
[C:1]([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=4)[CH:19]=[N:18]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]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=4)[CH:19]=[N:18]3)[N:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71279780N-tert-butyl-2-(6-methoxy-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Produkt 1

HCID 712797232-(6-methoxy-indazol-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamideAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of N-tert-butyl-2-(6-methoxy-1H-indazol-1-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (130 mg, 263 μmol) in dichloromethane (3 mL) was added trifluoroacetic acid (1 mL). After 15 h, the mixture was concentrated in vacuo, add 25 mL Jan. 10, 1960 mixture of ammonium hydroxide/methanol/dichloromethane, stir for 1 hour. concentrated in vacuo. Purification by chromatography (silica, 24 g Analogix column, 0-4% methanol containing 10% ammonium hydroxide in dichloromethane) gave 2-(6-methoxy-indazol-1-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (63 mg, 66%). MS (M+H)+=365; 1H NMR (DMSO-d6) δ: 8.92 (s, 1H), 8.40 (d, J=5.1 Hz, 2H), 8.01 (s, 1H), 7.85 (d, J=8.9 Hz, 1H), 7.67 (s, 1H), 7.07 (dd, J=8.9, 2.0 Hz, 1H), 3.91 (s, 3H), 1.46 (s, 9H).

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. additionadd 25 mL Jan
  3. addition10, 1960 mixture of ammonium hydroxide/methanol/dichloromethane
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography (silica, 24 g Analogix column, 0-4% methanol containing 10% ammonium hydroxide in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-f863736c5e564053af26baba10edc6e6
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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