1H-Indazol-6-amine → 2-Chloro-N-(1H-indazol-6-yl)-5-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 645695

Reaktionsgleichung

[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1.[NH2:23][C:24]1[CH:32]=[C:31]2[C:27]([CH:28]=[N:29][NH:30]2)=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C>C(O)CCC.C(OC(=O)C)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:23][C:24]2[CH:32]=[C:31]3[C:27]([CH:28]=[N:29][NH:30]3)=[CH:26][CH:25]=2)[C:5]2[C:10]([CH3:11])=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]=2[N:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To a solution of 2,4-dichloro-5-methyl-7-tosyl-pyrrolo[2,3-d]pyrimidine (0.36 g, 1 mmol) in n-butyl alcohol (3 mL) was added 6-aminoindazole (0.27 g, 2 mmol) and DIPEA (0.27 mL, 1.5 mmol) at room temperature. After heating at 90° C. for 4 h, the mixture was diluted with ethylacetate and the organic layer was sequentially washed with 1N HCl, saturated NaHCO3, and brine. The organic extract was then dried over Na2SO4 and concentrated to give a crude residue, which was purified by flash column (Hex/EtOAc=1:1) to give 2-Chloro-N-(1H-indazol-6-yl)-5-methyl-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.18 g).

Aufarbeitung

washthe organic layer was sequentially washed with 1N HCl, saturated NaHCO3, and brine
extractionThe organic extract
dry with materialwas then dried over Na2SO4
concentrationconcentrated
customto give a crude residue, which
customwas purified by flash column (Hex/EtOAc=1:1)

Quellen und Nachweise

ORD-Eintrag: ord-05c1d9062c7f4ef0ab9e01e7fa29bed3
Quelldatensatz: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07705004B2

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