Diisopropylethylamine → HCID 86639881, Verbindung

HRID 2040807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2040807
O[C:2]1C(C)=CC(C(NO)=N)=C[C:3]=1OC.CC[N:17]([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19].[CH2:24]1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[C:57]([O:61][C:62](=[O:78])[CH2:63][CH2:64][C:65]1[C:70]([CH3:71])=[CH:69][C:68]([C:72](=[NH:75])[NH:73][OH:74])=[CH:67][C:66]=1[CH2:76][CH3:77])([CH3:60])([CH3:59])[CH3:58]>CN(C=O)C.O.C([O-])(O)=O.[Na+].O1CCOCC1>[C:57]([O:61][C:62](=[O:78])[CH2:63][CH2:64][C:65]1[C:70]([CH3:71])=[CH:69][C:68]([C:72]2[N:75]=[C:2]([C:3]3[CH:20]=[C:18]([CH3:19])[N:17]=[C:21]([CH2:22][CH3:24])[CH:23]=3)[O:74][N:73]=2)=[CH:67][C:66]=1[CH2:76][CH3:77])([CH3:60])([CH3:59])[CH3:58]

Komponenten

9

Edukt 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 178436624tert-butyl 3-[2-ethyl-4-[(Z)-N'-hydroxycarbamimidoyl]-6-methylphenyl]propanoateHCID 178492423HCID 178492423, Verbindung

Produkt 1

HCID 86639881HCID 86639881, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 312751,4-DioxaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of isonicotinic acid 4 (100 mg, 0.496 mmol) and DIPEA (193 mg, 1.49 mmol) in DMF (2 mL), PyBOP (273 mg, 0.525 mmol) is added at 0° C. The mixture is stirred at 0° C. for 15 min before 3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenyl]-propionic acid tert-butyl ester (152 mg, 0.496 mmol) is added. The mixture is stirred at rt for 1 h before it is diluted with water and aq. NaHCO3 solution. The mixture is extracted twice with ether. The combined org. extracts are dried over MgSO4, filtered and concentrated to give the crude hydroxyamidine ester intermediate (420 mg); LC-MS: tR=0.90 min, [M+1]+=454.47. This material is dissolved in dioxane and then stirred at 80° C. for 5 h. The solvent is evaporated to give crude 3-{2-ethyl-4-[5-(2-ethyl-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenyl}-propionic acid tert. butyl ester; LC-MS: tR=1.07 min, [M+1]+=436.25.

Aufarbeitung

  1. additionis added
  2. extractionThe mixture is extracted twice with ether
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude hydroxyamidine ester intermediate (420 mg)
  7. stirringstirred at 80° C. for 5 h
  8. customThe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-9e41e8df5e26467e93a99878487e015a
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580824B2

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