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1,1'-Carbonyldiimidazole → (R)-(3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidin-1-yl)(4,4-difluoropiperidin-1-yl)methanone

HRID 1969741
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1969741
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH2:3]1.C1N=CN([C:25]([N:27]2[CH:31]=N[CH:29]=[CH:28]2)=[O:26])C=1.Cl.[F:33][C:34]1([F:40])CCNC[CH2:35]1>N1C=CC=CC=1>[C:8]1([C@@H:4]2[CH2:5][CH2:6][CH2:7][N:2]([C:25]([N:27]3[CH2:28][CH2:29][C:34]([F:40])([F:33])[CH2:35][CH2:31]3)=[O:26])[CH2:3]2)[N:12]2[C:13]3[CH:19]=[CH:18][NH:17][C:14]=3[N:15]=[CH:16][C:11]2=[CH:10][N:9]=1
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Komponenten

5

Edukt 3

HCID 682631,1'-Carbonyldiimidazole2×HCID 27583514,4-Difluoropiperidine hydrochlorideHCID 67216656(R)-1-(piperidin-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride

Produkt 1

HCID 58557191(R)-(3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidin-1-yl)(4,4-difluoropiperidin-1-yl)methanoneAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049
Pyridine
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of (R)-1-(piperidin-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride (0.24 g, 0.76 mmol) in pyridine (7.2 mL) was added CDI (0.14 g, 0.87 mmol) and the reaction mixture was stirred at about 50° C. for about 2 h. Additional CDI (0.02 g, 0.14 mmol) was added and the reaction mixture was stirred for about 1 h. To the reaction mixture was added 4,4-difluoropiperidine hydrochloride (0.12 g, 0.76 mmol). The reaction mixture was heated to about 55° C. for about 1 h, cooled to ambient temperature, and stirred for about 2 d. The solvent was removed under reduced pressure and the crude residue dissolved with DCM (5 mL) and washed with water (2 mL). The aqueous layer was back extracted with DCM (2 mL). The combined organic extracts were washed with brine (3 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0-5% MeOH in DCM to afford (R)-(3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidin-1-yl)(4,4-difluoropiperidin-1-yl)methanone (0.146 g, 49%) as an off white solid: LC/MS (Table 1, Method b) Rt=1.70 min; MS m/z: 389 (M+H)+.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for about 1 h
  2. temperatureThe reaction mixture was heated to about 55° C. for about 1 h
  3. temperaturecooled to ambient temperature
  4. stirringstirred for about 2 d
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe crude residue dissolved with DCM (5 mL)
  7. washwashed with water (2 mL)
  8. extractionThe aqueous layer was back extracted with DCM (2 mL)
  9. washThe combined organic extracts were washed with brine (3 mL)
  10. dry with materialdried over anhydrous MgSO4
  11. filtrationfiltered
  12. customThe crude material was purified by silica gel chromatography
  13. washeluting with a gradient of 0-5% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-a5a5e04237d642bc8256814e749c3ea5
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08426411B2

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