4-Methylmorpholine → N-(2-aminophenyl)-5-[3-(1,3-benzodioxol-5-yl)prop-2-enoyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

HRID 2093075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2093075
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[CH:11][C:12]([OH:14])=O)=[CH:9][C:4]=2[O:3][CH2:2]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.CN1CCOCC1.[NH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[NH:50][C:51]([C:53]1[S:54][C:55]2[CH2:56][NH:57][CH2:58][CH2:59][C:60]=2[N:61]=1)=[O:52]>CN(C=O)C>[NH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[NH:50][C:51]([C:53]1[S:54][C:55]2[CH2:56][N:57]([C:12](=[O:14])[CH:11]=[CH:10][C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)[CH2:58][CH2:59][C:60]=2[N:61]=1)=[O:52]

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 169173-(1,3-Benzodioxol-5-yl)prop-2-enoic acidHCID 757711-HydroxybenzotriazoleHCID 58117006N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

Produkt 1

HCID 66864671N-(2-aminophenyl)-5-[3-(1,3-benzodioxol-5-yl)prop-2-enoyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To the solution of 3-Benzo[1,3]dioxol-5-yl-acrylic acid (1.0 mmol) in dry 10 mL DMF, were added 1-hydroxybenzotriazole (1.2 mmol), 1 ethyl 3(3′ dimethylaminopropyl)carbodiimide (2 mmol) and N-methylmorpholine (2.0 mmol). Solution was cooled to 0° C. N-(2-aminophenyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxamide obtained from step VIII of example I was then added and mixture was stirred at room temperature overnight. Reaction mixture was concentrated, diluted with water, extracted with dichloromethane washed with brine solution, and dried over anhydrous Na2SO4. Concentrated and purified by column chromatography to get the title compound.

Aufarbeitung

  1. customReaction mixture
  2. concentrationwas concentrated
  3. additiondiluted with water
  4. extractionextracted with dichloromethane
  5. washwashed with brine solution
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationConcentrated
  8. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8679bbb9f025467f9615bf3e64fd82aa
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440830B2

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