Ammonia → HCID 58356335, Verbindung

HRID 244720

Reaktionsgleichung

Reaktionsgleichung von HRID 244720
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.ClC(N(C)C)=C(C)C.CCN(C(C)C)C(C)C.[NH:27]1[C:35]2[C:30](=[C:31]([C:36]3[CH:37]=[C:38]([NH2:51])[C:39]4[C:43]([CH:44]=3)=[N:42][N:41](C3CCCCO3)[CH:40]=4)[CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28]1.CC1C=CC(S(O)(=O)=O)=CC=1.N>C1COCC1.CO>[NH:27]1[C:35]2[C:30](=[C:31]([C:36]3[CH:44]=[C:43]4[C:39]([CH:40]=[N:41][NH:42]4)=[C:38]([NH:51][C:7]([C:4]4[CH:3]=[C:2]([CH3:1])[O:6][N:5]=4)=[O:9])[CH:37]=3)[CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28]1

Komponenten

9

Edukt 6

HCID 222AmmoniaHCID 6101p-Toluenesulfonic acidHCID 769473-Methyl-5-isoxazolecarboxylic acidHCID 81531DiisopropylethylamineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 582679956-(1H-Indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine

Produkt 1

HCID 58356335HCID 58356335, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

5-Methyl-3-isoxazolecarboxylic acid (21 mg) was treated with anhydrous THF (2 ml) and then 1-chloro-N,N,2-trimethylpropenylamine (0.026 ml). The reaction was stirred at RT under nitrogen for 2 h. The reaction was then treated with anhydrous DIPEA (0.131 ml) and 2 ml of solution of 6-(1H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (750 mg) in THF (30 ml). The reaction was then stirred at RT under nitrogen for 69 h. The solvent was blown off under a stream of nitrogen, dissolved in methanol (3 ml) and then the solvent removed under reduced pressure. The crude reaction mixture was dissolved in methanol (5 ml), treated with macroporous tosic acid resin (102 mg; 4.45 mmol/g) stirred at RT for 17 h and then treated with 0.88 ammonia (0.5 ml), stirred for 30 min and then filtered. The solvent was removed under reduced pressure and then purified by mass directed preparative HPLC (Method A) to give the title compound.

Aufarbeitung

  1. stirringThe reaction was then stirred at RT under nitrogen for 69 h
  2. customthe solvent removed under reduced pressure
  3. customThe crude reaction mixture
  4. stirringstirred at RT for 17 h
  5. stirringstirred for 30 min
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. custompurified by mass

Quellen und Nachweise

ORD-Eintrag
ord-9f851daf79ec436992c3135020aa2f7b
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658635B2

Verknüpfte Notizen

Wird geladen…