Trifluoroacetic acid → 2-(1-(5-Methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole

HRID 1429558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1429558
[CH3:1][C:2]1[S:6][C:5]([N:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[S:15][C:16]4[CH:22]=[C:21]([C:23]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH:24]=5)[CH:20]=[CH:19][C:17]=4[N:18]=3)[CH2:9][CH2:8]2)=[N:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[S:6][C:5]([N:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[S:15][C:16]4[CH:22]=[C:21]([C:23]5[CH2:28][CH2:27][NH:26][CH2:25][CH:24]=5)[CH:20]=[CH:19][C:17]=4[N:18]=3)[CH2:9][CH2:8]2)=[N:4][N:3]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67468486tert-butyl 4-(2-(1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Produkt 1

HCID 674670502-(1-(5-Methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazoleAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of tert-butyl 4-(2-(1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (443 mg, 0.862 mmol) in CH2Cl2 (7 mL) at rt was added TFA (1.0 mL, 13 mmol). The reaction mixture was stirred at rt overnight. The mixture was diluted with CH2Cl2 (10 mL), washed with aq. NaOH (1 N, 15 mL), then brine. The organic layer was dried (Na2SO4), filtered, and concentrated to afford 2-(1-(5-methyl-1,3,4-thiadiazol-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole (357 mg, 0.863 mmol, 100% yield) as a yellow solid. LCMS (m/z)=414 (M+H)+.

Aufarbeitung

  1. washwashed with aq. NaOH (1 N, 15 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b48221ac64b74735bc14c704d23f4c23
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940716B2

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