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1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-[4-(1-tert-Butoxycarbonyl-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-2-oxo-piperazin-1-ylmethyl]-pyrrolo[3,2-c]piperidine-1-carboxylic acid tert-butyl ester

HRID 1433027
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1433027
N12CCCN=C1CCCCC2.[C:12]([O:16][C:17]([N:19]1[C:27]2[CH:26]=[CH:25][N:24]=[CH:23][C:22]=2[CH:21]=[C:20]1[CH2:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36]#[C:37][C:38]2[CH:39]=[N:40][CH:41]=[CH:42][C:43]=2[NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:31][C:30]1=[O:52])=[O:18])([CH3:15])([CH3:14])[CH3:13]>CC#N>[C:12]([O:16][C:17]([N:19]1[C:27]2[CH2:26][CH2:25][NH:24][CH2:23][C:22]=2[CH:21]=[C:20]1[CH2:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36]2[N:44]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C:43]3[CH:42]=[CH:41][N:40]=[CH:39][C:38]=3[CH:37]=2)[CH2:31][C:30]1=[O:52])=[O:18])([CH3:15])([CH3:14])[CH3:13]
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Komponenten

4

Edukt 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54474940HCID 54474940, Verbindung

Produkt 1

HCID 690244022-[4-(1-tert-Butoxycarbonyl-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-2-oxo-piperazin-1-ylmethyl]-pyrrolo[3,2-c]piperidine-1-carboxylic acid tert-butyl esterAusbeute 107,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

1,8-Diazabicyclo[5.4.0]undec-7-ene (42 mg, 0.27 mmol) is added to a suspension containing 2-{4-[3-(4-tert-butoxycarbonylamino-pyridin-3-yl)-prop-2-ynyl]-2-oxo-piperazin-1-ylmethyl}-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (77 mg, 0.14 mmol) in anhydrous CH3CN (10 mL) and the mixture is warmed to 50° C. After 4 h, the reaction mixture is concentrated to dryness and the residue is partitioned between CH2Cl2 (50 mL) and water (50 mL) and the layers are separated. The aqueous layer is extracted twice with CH2Cl2 (25 mL) and the combined organic phase is washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to provide 85 mg of the title compound as a crude solid which is used directly without further purification. 1H NMR (300 MHz, CDCl3) δ1.68 (s, 9H), 1.70 (s, 9H), 2.91 (m, 2H), 3.41 (s, 2H), 3.49 (m, 2H), 4.26 (s, 2H), 4.95 (d, J=1.1 Hz, 2H), 6.39 (d, J=0.7 Hz, 1H), 6.68 (d, J=0.7 Hz, 1H), 7.86 (m, 1H), 8.41 (m, 1H), 8.76 (br s, 1H), 8.82 (br s, 1H) ppm: MS (EI): m/z 561 (M+H).

Aufarbeitung

  1. concentrationthe reaction mixture is concentrated to dryness
  2. customthe residue is partitioned between CH2Cl2 (50 mL) and water (50 mL)
  3. customthe layers are separated
  4. extractionThe aqueous layer is extracted twice with CH2Cl2 (25 mL)
  5. washthe combined organic phase is washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4049fceebd004427b743f968594249e8
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07612075B2

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