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Hydrochloric Acid → ((R)-1-Phenyl-ethyl)-[6-(4-piperazin-1-ylmethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

HRID 2252794
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2252794
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[NH:38][C:24]4[N:25]=[CH:26][N:27]=[C:28]([NH:29][C@@H:30]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[CH3:31])[C:23]=4[CH:22]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1.CO>[C:32]1([C@H:30]([NH:29][C:28]2[C:23]3[CH:22]=[C:21]([C:18]4[CH:19]=[CH:20][C:15]([CH2:14][N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[CH:16][CH:17]=4)[NH:38][C:24]=3[N:25]=[CH:26][N:27]=2)[CH3:31])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 59645279HCID 59645279, Verbindung

Produkt 1

HCID 11350462((R)-1-Phenyl-ethyl)-[6-(4-piperazin-1-ylmethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

4-{4-[4-((R)-1-Phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzyl}-piperazine-1-carboxylic acid tert-butyl ester (1.8 g, 3.5 mmol) is dissolved in 150 mL of dioxane by gentle warming. To this solution is added a solution of 4 N hydrochloric acid in dioxane (Aldrich, Buchs, Switzerland) (5 mL, 20 mmol) and the mixture stirred at 50 to 60° C. for 1 hour. The resulting suspension is diluted with 75 mL of methanol and stirred for 1 additional hour under reflux after which the mixture is cooled and the solvent evaporated. The residue is dissolved in diluted hydrochloric acid and washed with ethyl acetate. The aqueous phase is treated with solid potassium carbonate until basic and evaporated. The residue which contains inorganic salts is purified by flash chromatography using dichloromethane/methanol 7:3 containing 1% conc. ammonia. Pure fractions were taken up in ethyl acetate, washed with water and brine, dried with sodium sulfate and evaporated to give the title compound as a solid; m.p. 240-242° C.; MS-ES+: (M+H)+=413; TLC Rf(dichloromethane/methanol 7:3 containing 1% conc. ammonia) 0.35; HPLC tR=6.86 min.

Aufarbeitung

  1. stirringstirred for 1 additional hour
  2. temperatureunder reflux after which the mixture
  3. temperatureis cooled
  4. customthe solvent evaporated
  5. dissolutionThe residue is dissolved in diluted hydrochloric acid
  6. washwashed with ethyl acetate
  7. additionThe aqueous phase is treated with solid potassium carbonate until basic and
  8. customevaporated
  9. customis purified by flash chromatography
  10. washwashed with water and brine
  11. dry with materialdried with sodium sulfate
  12. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-945d69409ef64c2ab77ead963c2f4839
Quelldatensatz
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07323469B2

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