Potassium Carbonate → HCID 117729754, Verbindung

HRID 60659

Reaktionsgleichung

[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[C:16]([Cl:18])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I>[NH2:10][C:8]1[N:7]([C:12]2[CH:13]=[C:14]([OH:19])[CH:15]=[C:16]([Cl:18])[CH:17]=2)[N:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A microwave vial containing 3-tert butyl-1h-pyrazol-5-amine (559 mg, 4.02 mmol), Intermediate 62a (1.00 g, 4.82 mmol), copper(I) iodide (38 mg, 0.20 mmol) and potassium carbonate (1.16 g, 8.44 mmol) was repeatedly purged with argon. Trans-N,N′-dimethylcyclohexane-1,2-diamine (126 μL, 0.80 mmol) was added and the mixture was re-purged with argon. Degassed toluene (4 mL) was added and the resulting suspension was stirred and heated at 110° C. for 24 h. The cooled suspension was passed through Celite pad and diluted with water and extracted with EtOAc. The combined organics were dried and concentrated in vacuo. The residue was purified by FCC, using 0-50% EtOAc in cyclohexane, to give the title compound (620 mg, 62%). LCMS (Method 3): Rt 3.13 min, m/z 266 [MH+].

Aufarbeitung

customwas repeatedly purged with argon
customthe mixture was re-purged with argon
additionDegassed toluene (4 mL) was added
additiondiluted with water
extractionextracted with EtOAc
customThe combined organics were dried
concentrationconcentrated in vacuo
customThe residue was purified by FCC

Quellen und Nachweise

ORD-Eintrag: ord-c7423d7095ec4c6a83aa424725e57a0d
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09440974B2

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