Triethylamine → HCID 67959705, Verbindung

HRID 1529297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1529297
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]4[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=4[F:24])[CH:15]=3)[N:10](C(OC(C)(C)C)=O)[CH:9]=2)[CH:5]=[N:4][CH:3]=1.CC[N:34]([CH2:37][CH3:38])[CH2:35][CH3:36].[CH3:39][N:40]1C(=O)CCC1>C(Cl)Cl.O>[F:23][C:22]1[CH:21]=[CH:20][CH:19]=[C:18]([F:24])[C:17]=1[C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[C:6]1[N:7]=[C:2]([N:34]2[CH2:35][CH2:36][CH:39]([NH2:40])[CH2:38][CH2:37]2)[CH:3]=[N:4][CH:5]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 86709767HCID 86709767, Verbindung

Produkt 1

HCID 67959705HCID 67959705, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A glass microwave reaction vessel was charged with tert-butyl 3-(6-chloropyrazin-2-yl)-5-(2,6-difluorophenyl)-1H-indole-1-carboxylate (50.0 mg, 0.113 mmol) and 4-boc-amino-1-piperidine (34.0 mg, 0.170 mmol) in NMP (0.6 mL), followed by Et3N (0.047 mL, 0.339 mmol). The reaction mixture was stirred and heated in an oil bath at 150° C. for 16 h, and then the mixture was diluted with DCM and water. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The residue was dissolved in DCM (2 mL) and treated with TFA (0.5 mL). The reaction mixture was stirred at RT for 2 h, and solvent was removed. The residue was purified with RP-HPLC to give 1-(6-(5-(2,6-difluorophenyl)-1H-indol-3-yl)pyrazin-2-yl)piperidin-4-amine as a brown solid. MS (ESI, pos. ion) m/z: 406 (M+1).

Aufarbeitung

  1. customA glass microwave reaction vessel
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in DCM (2 mL)
  7. additiontreated with TFA (0.5 mL)
  8. stirringThe reaction mixture was stirred at RT for 2 h
  9. customsolvent was removed
  10. customThe residue was purified with RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c19067c2b6d1447bb7a65f73b4e59bad
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090593B2

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