Hydrochloric Acid → (R)-6-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)-N-(piperidin-3-yl)pyrazin-2-amine

HRID 1529314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1529314
[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[C:20]2[N:25]=[C:24]([NH:26][C@@H:27]3[CH2:32][CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28]3)[CH:23]=[N:22][CH:21]=2)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2].Cl>CCOC(C)=O>[CH:1]([O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[C:20]2[N:25]=[C:24]([NH:26][C@@H:27]3[CH2:32][CH2:31][CH2:30][NH:29][CH2:28]3)[CH:23]=[N:22][CH:21]=2)[CH:8]=[N:7][CH:6]=1)([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 67960038(R)-tert-butyl 3-(6-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)pyrazin-2-ylamino)piperidine-1-carboxylate

Produkt 1

HCID 67959856(R)-6-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)-N-(piperidin-3-yl)pyrazin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of (R)-tert-butyl 3-(6-(5-(6-isopropoxy-pyrazin-2-yl)-1-tosyl-1H-indol-3-yl)pyrazin-2-ylamino)piperidine-1-carboxylate (0.250 g, 0.365 mmol) in 1-4-dioxane (3.6 mL), 1N NaOH (3.6 mL) was added and heated at 100° C. for 2 h. The reaction mixture was quenched with ice cold water and precipitate was formed. The precipitate was collected by filtration, washed with ice cold water and dried to give pure (R)-tert-butyl 3-(6-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)pyrazin-2-ylamino)piperidine-1-carboxylate (180 mg, 93%). MS (ESI, pos. ion) m/z: 530.0 (M+1). To a solution of (R)-tert-butyl 3-(6-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)pyrazin-2-ylamino)piperidine-1-carboxylate (180 mg, 1.25 mmol) in EtOAc (5.0 mL) was treated with HCl in EtOAc (5.0 mL) and stirred at RT for 3 h. The reaction mixture was quenched with water, neutralized with NaHCO3, extracted with EtOAc. The organic layer was separated, dried over Na2SO4 and evaporated to dryness. The crude solid was re-crystallized in acetone to obtain (R)-6-(5-(6-isopropoxypyrazin-2-yl)-1H-indol-3-yl)-N-(piperidin-3-yl)pyrazin-2-amine. MS (ESI, pos. ion) m/z: 430.0 (M+1).

Aufarbeitung

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude solid was re-crystallized in acetone

Quellen und Nachweise

ORD-Eintrag
ord-e7a978a98ea74db19f228d3c5f75c608
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090593B2

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