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Cesium carbonate → HCID 68313011, Verbindung

HRID 1530443
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1530443
C(OC(N1CCC(C([O:20][C:21]2[CH:43]=[CH:42][C:24]3[C:25]4[N:29]([CH2:30][CH2:31][O:32][C:23]=3[CH:22]=2)[CH:28]=[C:27]([C:33]2[N:34]([CH:39]([CH3:41])[CH3:40])[N:35]=[C:36]([CH3:38])[N:37]=2)[N:26]=4)CC)CC1)=O)C1C=CC=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:50]([O:52][C:53](=[O:64])[CH:54](Br)[CH2:55][CH:56]([CH3:62])[C:57]([O:59][CH2:60][CH3:61])=[O:58])[CH3:51]>CC#N>[CH2:50]([O:52][C:53](=[O:64])[CH:54]([O:20][C:21]1[CH:43]=[CH:42][C:24]2[C:25]3[N:29]([CH2:30][CH2:31][O:32][C:23]=2[CH:22]=1)[CH:28]=[C:27]([C:33]1[N:34]([CH:39]([CH3:41])[CH3:40])[N:35]=[C:36]([CH3:38])[N:37]=1)[N:26]=3)[CH2:55][CH:56]([CH3:62])[C:57]([O:59][CH2:60][CH3:61])=[O:58])[CH3:51]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 68312705HCID 68312705, VerbindungHCID 86671456HCID 86671456, Verbindung

Produkt 1

HCID 68313011HCID 68313011, VerbindungAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a suspension of 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-ol from Example 4 (330 mg, 1.013 mmol) in CH3CN (18 mL) was added Cs2CO3 (825 mg, 2.53 mmol) followed by a solution of 2-bromo-4-methylpentanedioic acid diethyl ester (640 mg, 2.276 mmol) in CH3CN (2 mL) and stirring at reflux temperature was continued for 1.5 h. After cooling to RT, the reaction mixture was partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc and the combined organic layers were washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-8% MeOH in DCM) affording 2-[2-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]-4-methylpentanedioic acid diethyl ester as a pale yellow gum (391 mg, 73%). LCMS: RT 3.59 min [M+H]+ 526.5

Aufarbeitung

  1. temperatureat reflux temperature
  2. customthe reaction mixture was partitioned between water and EtOAc
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washthe combined organic layers were washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 2-8% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-52f5f05338ef470a842997d0b0f9dc53
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090628B2

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