Acetic Acid → 1-{4-[(Thiophen-3-ylmethyl)amino]phenyl}-butan-1-one

HRID 593298

Reaktionsgleichung

Reaktionsgleichung von HRID 593298
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[S:13]1[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14]1.C(O)(=O)C>C(Cl)Cl.CO.CC(N(C)C)=O>[S:13]1[CH:17]=[CH:16][C:15]([CH2:18][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8](=[O:12])[CH2:9][CH2:10][CH3:11])=[CH:6][CH:7]=2)=[CH:14]1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 155271-Butanone, 1-(4-aminophenyl)-HCID 681353-Thiophenecarboxaldehyde

Produkt 1

HCID 251271501-{4-[(Thiophen-3-ylmethyl)amino]phenyl}-butan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 31374DimethylacetamideLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

In a 20 mL vial, to a solution of 1-(4-aminophenyl)-butan-1-one (19.64 mg, 0.1 mmol) in DCM/MeOH (0.7 mL) was added a solution of thiophene-3-carbaldehyde (22.4 mg, 0.2 mmol) in DMA (0.8 mL). A solution of acetic acid (18 mg, 0.3 mmol) in DCM/MeOH (0.7 mL) was added, followed by the addition of 160 mg of MP-CNBH3 resin (3 eq.; subst. 2.25 mmoles/g). The vial was capped and was then heated with shaking overnight at 55° C. The progress of the reaction was monitored by LC/MS. After completion of the reaction, the reaction mixture was concentrated to dryness. The residue was dissolved in 1:1 DMSO/MeOH. Purification by reverse phase HPLC (TFA method) gave the title compound.

Aufarbeitung

  1. customThe vial was capped
  2. temperaturewas then heated
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated to dryness
  5. dissolutionThe residue was dissolved in 1:1 DMSO/MeOH
  6. customPurification by reverse phase HPLC (TFA method)

Quellen und Nachweise

ORD-Eintrag
ord-e90a9289aeec45d7859d29bd7bf3c7e6
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242933B2

Verknüpfte Notizen

Wird geladen…