Hydrochloric Acid → methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate

HRID 1518266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518266
Cl.Cl.[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[CH2:23][NH:22][CH2:21][CH2:20]2)=[O:14].Cl[C:26]1[S:27][CH:28]=[C:29]([C:31]([O:33][CH3:34])=[O:32])[N:30]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl>CC(N(C)C)=O>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C:13]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[CH2:23][N:22]([C:26]1[S:27][CH:28]=[C:29]([C:31]([O:33][CH3:34])=[O:32])[N:30]=1)[CH2:21][CH2:20]2)=[O:14]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 7213135Methyl 2-chloro-4-thiazolecarboxylateHCID 86644320N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide dihydrochloride

Produkt 1

HCID 59447460methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylateAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydroisoquinoline-8-carboxamide dihydrochloride (1B) (5.3 g, 13.86 mmol) and methyl 2-chlorothiazole-4-carboxylate (2.5 g, 14 mmol) in DMA (60 mL) was added Cs2CO3 (25 g, 70 mmol). The reaction mixture was stirred at 50° C. overnight. The reaction mixture was cooled to rt, acidified with 5% HCl, extracted with DCM, washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with 5% MeOH in DCM to provide 4.2 g (67%) of the desired product methyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)thiazole-4-carboxylate (1C): LC/MS (APCI): m/z 451.0 (M+H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with DCM
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by column chromatography on silica gel eluting with 5% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-fdab4d4e8d3e4c69b52d9bbe6aa52d7b
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232273B2

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