3-Cyanobenzoic acid → 3-Cyanobenzamide

HRID 1478136

Reaktionsgleichung

Reaktionsgleichung von HRID 1478136
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](O)=[O:7])#[N:2].C1C=CC2N(O)N=[N:18]C=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH2:18])=[O:7])#[N:2]

Komponenten

6

Edukt 4

HCID 158753-Cyanobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 769743-Cyanobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-Cyano-benzoic acid (1.2 eq), the amine derivative (1 eq), HOBt (1.2 eq), DIEA (1.2 eq) and EDCI.HCl (1.2 eq) were dissolved in dry DMF (0.15 M), under argon. The mixture was stirred at room temperature overnight. DMF is evaporated and saturated NaHCO3 solution was added. Product was extracted with EtOAc, dried over Na2SO4, filtered and evaporated. The crude was purified on reverse phase (H2O 1% TFA/MeCN 1% TFA 100/0, 0/100). MeCN was evaporated. The product was suspended in H2O and basified with saturated NaHCO3 solution until pH=8-9. The aqueous layer was extracted three times with AcOEt. The organic layer was evaporated to give the final compound.

Aufarbeitung

  1. customDMF is evaporated
  2. additionsaturated NaHCO3 solution was added
  3. extractionProduct was extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude was purified on reverse phase (H2O 1% TFA/MeCN 1% TFA 100/0, 0/100)
  8. customMeCN was evaporated
  9. extractionThe aqueous layer was extracted three times with AcOEt
  10. customThe organic layer was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-bf112b8945d844e1b28b49aa37997539
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403823B2

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