Carbamate → 5-(Quinolin-5-ylcarbamoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid

HRID 2093055Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2093055
Cl.C([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])C.CCN(CC)CC.[C:23](=[O:26])([O-])[NH2:24].[CH:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][N:28]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CO.O>[N:28]1[C:27]2[C:36](=[C:35]([NH:24][C:23]([N:11]3[CH2:12][CH2:13][C:14]4[N:15]=[C:7]([C:5]([OH:4])=[O:6])[S:8][C:9]=4[CH2:10]3)=[O:26])[CH:34]=[CH:33][CH:32]=2)[CH:31]=[CH:30][CH:29]=1

Komponenten

10

Edukt 6

HCID 276CarbamateHCID 313Hydrochloric AcidHCID 8405IsoquinolineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 53393419Ethyl 4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine-2-carboxylate

Produkt 1

HCID 668650425-(Quinolin-5-ylcarbamoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

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 (1.0 eq) in DMF was added Et3N (1.0 eq.) followed by carbamate derivative of Isoquinoline (1.0 eq) obtained in step I above. The reaction mixture was refluxed for 3 h at 90° C. Water was added and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, was hydrolysed by stirring in MeOH: water and K2CO3 (2.0 eq.) for 48 h Reaction mixture was concentrated under reduced pressure and neutralized to pH 7.0 to afford 5-(Quinolin-5-ylcarbamoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid).

Aufarbeitung

  1. customthe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto afford crude product, which
  5. concentrationwas concentrated under reduced pressure and neutralized to pH 7.0

Quellen und Nachweise

ORD-Eintrag
ord-03ac15654a1a4d8daa08631d22333b15
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440830B2

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