Hydrochloric Acid → HCID 57594292, Verbindung

HRID 730339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 730339
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C@@H:13]([NH:33][C:34](=[O:40])OC(C)(C)C)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:22]=[C:23]3[C:28]([CH:29]([OH:31])[CH3:30])=[CH:27][CH:26]=[CH:25][N:24]3[CH:32]=2)=[CH:17][CH:16]=1.Cl.O1CCOCC1.C(N(CC)C(C)C)(C)C.[Cl:57][C:58]1[CH:59]=[C:60]([CH:75]=[CH:76][C:77]=1[O:78][CH:79]([CH3:81])[CH3:80])C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O>O>[Cl:57][C:58]1[CH:59]=[C:60]([CH:75]=[CH:76][C:77]=1[O:78][CH:79]([CH3:81])[CH3:80])[C:34]([NH:33][C@@H:13]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:22]=[C:23]3[C:28]([CH:29]([OH:31])[CH3:30])=[CH:27][CH:26]=[CH:25][N:24]3[CH:32]=2)=[CH:17][CH:16]=1)[CH2:12][N:3]1[C:2](=[O:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=[O:11])=[O:40]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 57594128HCID 57594128, VerbindungHCID 575943381,1-Dimethylethyl [(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)ethyl]carbamate

Produkt 1

HCID 57594292HCID 57594292, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 1,1-dimethylethyl [(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-({4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-2-yl]phenyl}methyl)ethyl]carbamate (1.79 g, 3.31 mmol) and 4 M HCl in 1,4-dioxane (20 mL, 80 mmol) was stirred at room temperature for 45 minutes. The reaction was concentrated to dryness and redissolved in DMF (30 mL). To this solution was added N,N-diisopropylethylamine (2.14 g, 16.55 mmol) and pentafluorophenyl 3-chloro-4 [(1-methylethyl)oxy]benzoate (1.36 g, 3.31 mmol). The mixture was stirred overnight at room temperature, diluted with water, and extracted into ethyl acetate. The extracts were washed with water, dried (Na2SO4), and concentrated in vacuo to give the title compound (2.10 g, 100%) as a tan solid. MS(ES+) m/e 637 [M+H]+.

Aufarbeitung

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutionredissolved in DMF (30 mL)
  3. stirringThe mixture was stirred overnight at room temperature
  4. extractionextracted into ethyl acetate
  5. washThe extracts were washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-23c20b8926fd48ed9ebaf1b20c8e5cae
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582668B2

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