Triethylamine → HCID 178434253, Verbindung

HRID 643346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643346
[NH2:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:10]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:9]2)=[N:6][C:5](Br)=[CH:4][N:3]=1.[CH3:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([Sn](C)(C)C)[CH:37]=2)[NH:32][N:31]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:10]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:9]2)=[N:6][C:5]([C:36]2[CH:37]=[C:38]3[C:33](=[CH:34][CH:35]=2)[NH:32][N:31]=[C:30]3[CH3:29])=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 592622472-amino-5-bromo-3-[(S)-4-Boc-3-benzylpiperazinyl]pyrazineHCID 178434313HCID 178434313, Verbindung

Produkt 1

HCID 178434253HCID 178434253, VerbindungAusbeute 70,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of -amino-5-bromo-3-[(S)-4-Boc-3-benzylpiperazinyl]pyrazine 108 (100 mg, 0.223 mmol) and 3-methyl-5-trimethylstannanyl-1H-indazole 105 (66 mg, 0.223 mmol.) in DMF (3.5 mL) was added tris(dibenzylideneacetone)bipalladium (10 mg, 0.011 mmol), tri-o-tolylphosphine (7 mg, 0.023 mmol) and triethylamine (23 mg, 0.23 mmol). The reaction mixture was heated in a microwave reactor at 120° C. for 10 minutes. Ethyl acetate (100 mL) was added. The organic layer was washed with water and brine. The organic layer was dried over sodium sulfate and filtered through Celite. The organic solvent was evaporated under reduced pressure. The crude product was purified by RP-HPLC to yield the desired 2-amino-3-[(S)-4-Boc-3-benzylpiperazinyl]-5-(3-methyl-1H-indazol-5-yl)pyrazine 109 (79 mg, 0.158 mmol).

Aufarbeitung

  1. washThe organic layer was washed with water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered through Celite
  4. customThe organic solvent was evaporated under reduced pressure
  5. customThe crude product was purified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-bae172de31624776a06f45ae5abb7fdb
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700601B2

Notizen zur Reaktion

Wird geladen…