Ammonium Chloride → N-cyclopropyl-3-(1-(3-fluorophenyl)-7-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridin-4-ylamino)-4-methylbenzamide

HRID 659709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 659709
Cl[C:2]1[C:3]2[CH:12]=[N:11][N:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[C:4]=2[N:5]([CH3:9])[C:6](=[O:8])[CH:7]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.[NH2:48][C:49]1[CH:50]=[C:51]([CH:58]=[CH:59][C:60]=1[CH3:61])[C:52]([NH:54][CH:55]1[CH2:57][CH2:56]1)=[O:53].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl-].[NH4+]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:55]1([NH:54][C:52](=[O:53])[C:51]2[CH:58]=[CH:59][C:60]([CH3:61])=[C:49]([NH:48][C:2]3[C:3]4[CH:12]=[N:11][N:10]([C:13]5[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=5)[C:4]=4[N:5]([CH3:9])[C:6](=[O:8])[CH:7]=3)[CH:50]=2)[CH2:56][CH2:57]1

Komponenten

8

Edukt 5

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 119838543-amino-N-cyclopropyl-4-methylbenzamideHCID 57708073HCID 57708073, Verbindung

Produkt 1

HCID 25242389N-cyclopropyl-3-(1-(3-fluorophenyl)-7-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridin-4-ylamino)-4-methylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a glass tube, a mixture of 4-chloro-1-(3-fluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (76 mg, 0.27 mmol), tris(dibenzylideneacetone)dipalladium (0) (12 mg), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (Dave-Phos, 12 mg), 3-amino-N-cyclopropyl-4-methylbenzamide (78 mg, 0.41 mmol) in THF (2 mL) was de-gassed slightly under reduced pressure or a vacuum. LiHMDS (0.82 mL of 1.0 M in THF solution, 821 mmol) was added slowly. The glass tube was sealed and placed in an oil bath at 60° C. for 1 h. The mixture was cooled to RT and treated with saturated ammonium chloride solution, then extracted twice with EtOAc. The combined EtOAc layers were washed with brine, dried and concentrated. The resulting crude material was purified by silica gel chromatography (80-100% EtOAc in hexanes) to provide the title compound as a tan crystalline solid. MS (ESI, pos.ion) m/z: 432.0 (M+1).

Aufarbeitung

  1. customwas de-gassed slightly under reduced pressure
  2. customThe glass tube was sealed
  3. extractionextracted twice with EtOAc
  4. washThe combined EtOAc layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting crude material was purified by silica gel chromatography (80-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8460c7a31a044b79b2d89fae734e5775
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080546B2

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