Hydrochloric Acid → Ethyl 5-(anilinocarbonothioyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylate

HRID 2093063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2093063
Cl.[CH2:2]([O:4][C:5]([C:7]1[S:8][C:9]2[CH2:10][NH:11][CH2:12][CH2:13][C:14]=2[N:15]=1)=[O:6])[CH3:3].C(N(CC)CC)C.[C:23]1([N:29]=[C:30]=[S:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl.O>[NH:29]([C:30]([N:11]1[CH2:12][CH2:13][C:14]2[N:15]=[C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[S:8][C:9]=2[CH2:10]1)=[S:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7673Phenyl IsothiocyanateHCID 8471TriethylamineHCID 53393419Ethyl 4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine-2-carboxylate

Produkt 1

HCID 86650190Ethyl 5-(anilinocarbonothioyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

5-tert-butyl 2-ethyl 6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-2,5(4H)-dicarboxylate obtained in step V of example 1 was deprotected to get the hydrochloride salt of 4,5,6,7-Tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid ethyl ester. To a solution of a HCl salt of 4,5,6,7-Tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid ethyl ester (1 eq) in dichloromethane, triethyl amine (1.2 eq) was added at 0° C. and the reaction mixture was stirred for 15 min. To this, a solution of phenyl isothiocyanate (1 eq) in dichloromethane was added and the reaction was continued at room temperature for 3 h. Water was added and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded—ethyl 5-(anilinocarbonothioyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylate.

Aufarbeitung

  1. waitthe reaction was continued at room temperature for 3 h
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford crude product, which
  6. customon purification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-afa3dd686e7c41ad84adee35b07e3fb6
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440830B2

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