Hydrochloric Acid → N-(piperidin-4-yl)-6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]thiazole-2-carboxamide

HRID 1626339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626339
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([O:15][C:16]3[CH:40]=[CH:39][C:19]4[N:20]=[C:21]([C:23]([NH:25][CH:26]5[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]5)=[O:24])[S:22][C:18]=4[CH:17]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Cl>O1CCOCC1>[NH:29]1[CH2:30][CH2:31][CH:26]([NH:25][C:23]([C:21]2[S:22][C:18]3[CH:17]=[C:16]([O:15][CH:12]4[CH2:11][CH2:10][N:9]([C:6]5[CH:5]=[CH:4][C:3]([C:2]([F:42])([F:1])[F:41])=[CH:8][CH:7]=5)[CH2:14][CH2:13]4)[CH:40]=[CH:39][C:19]=3[N:20]=2)=[O:24])[CH2:27][CH2:28]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 57951083Tert-butyl 4-(6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]thiazole-2-carboxamido)piperidine-1-carboxylate2×

Produkt 1

HCID 57951054N-(piperidin-4-yl)-6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]thiazole-2-carboxamideAusbeute 110,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 4-(6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]thiazole-2-carboxamido)piperidine-1-carboxylate (compound 8) (0.16 g, 0.27 mmol) and 4N hydrochloric acid in dioxane (2 mL) was stirred at room temperature for 1 h. The reaction mixture was concentrated and washed with diethyl ether (2×3 mL) and then dried under reduced pressure to afford N-(piperidin-4-yl)-6-(1-(4-(trifluoromethyl)phenyl)piperidin-4-yloxy)benzo[d]thiazole-2-carboxamide as a off-white solid (0.15 g, 99%). 1H NMR (CD3OD, 300 MHz) 7.83 (m, 5H), 7.48 (s, 1H), 7.23 (m, 1H), 4.93 (m, 1H), 4.22 (m, 1H), 3.90 (m, 3H), 3.35 (m, 2H), 3.17 (m, 2H), 2.23 (m, 8H), 1.98 (m, 2H) ppm; MS (ES) 489.1 (M+1).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with diethyl ether (2×3 mL)
  3. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2e3ba2b7fa0e47ee8c6ec29255a9da5c
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785449B2

Notizen zur Reaktion

Wird geladen…