1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(3-Amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo(2.2.1)heptane

HRID 1775506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1775506
C[C:2]1([CH3:20])[CH2:15][N:14]2[C:5](=NC3C([C:13]2=O)=CC=C(C(O)=O)C=3)[CH2:4][CH2:3]1.[OH:21][NH:22][C:23](=[NH:30])C1C=CC=CN=1.CC[N:33]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH2:4]1[CH:3]2[CH:2]([C:20]3[O:21][N:22]=[C:23]([NH2:30])[N:33]=3)[CH2:15][N:14]([CH2:13]2)[CH2:5]1

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 711122258,8-dimethyl-11-oxo-7,8,9,11-tetrahydro-6H-pyrido[2,1-b]quinazoline-3-carboxylic acidHCID 178513306HCID 178513306, Verbindung

Produkt 1

HCID 1639383-(3-Amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo(2.2.1)heptane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of an acid (e.g., 8,8-dimethyl-11-oxo-7,8,9,11-tetrahydro-6H-pyrido[2,1-b]quinazoline-3-carboxylic acid, 1 equiv), N-hydroxypicolinimidamide (1.5 equiv), EDCI (1.5 equiv) and HOBt (1.5 equiv) in DMF was stirred at 80° C. overnight. The reaction was cooled to room temperature, then the reaction mixture was diluted with H2O and extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude residue was purified by preparative chromatography to give the desired oxadiazole-containing product (e.g., 8,8-dimethyl-3-(3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl)-6,7,8,9-tetrahydropyrido[2,1-b]quinazolin-11-one).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe crude residue was purified by preparative chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f69aaea2940d4d5e9d2c2cc08f3199b5
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260452B2

Notizen zur Reaktion

Wird geladen…