Trifluoroacetic acid → tert-butyl 5-((5-chloro-2-((1,5-dimethyl-1H-pyrazol-3-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 1478042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478042
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)[C:5]([Cl:24])=[CH:4][N:3]=1.[CH3:25][N:26]1[C:30]([CH3:31])=[CH:29][C:28]([NH2:32])=[N:27]1.FC(F)(F)C(O)=O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[Cl:24][C:5]1[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)=[N:7][C:2]([NH:32][C:28]2[CH:29]=[C:30]([CH3:31])[N:26]([CH3:25])[N:27]=2)=[N:3][CH:4]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 70177471,5-dimethyl-1H-pyrazol-3-amineHCID 118389983tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

Produkt 1

HCID 118389982tert-butyl 5-((5-chloro-2-((1,5-dimethyl-1H-pyrazol-3-yl)amino)pyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylateAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of tert-butyl 5-[(2,5-dichloropyrimidin-4-yl)amino]-hexahydro-1H-cyclopenta[c]pyrrole-2-carboxylate (1.29 g, 3.46 mmol) and 1,5-dimethylpyrazol-3-amine (0.80 g, 7.20 mmol) in 1,4-dioxane (20 mL) was added trifluoroacetic acid (2.01 g, 17.60 mmol). The reaction mixture was stirred at 100° C. overnight and adjusted to pH=10 with a saturated Na2CO3 solution, then extracted with EtOAc (100 mL×3). The combined organic phases were washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=2/1) to give the title compound as a yellow solid (294.5 mg, 19%).

Aufarbeitung

  1. extractionextracted with EtOAc (100 mL×3)
  2. washThe combined organic phases were washed with brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-1138b0d631604d2abfd24eb5c0a1a61a
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403801B2

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