Hydrochloric Acid → N-(Azetidin-3-yl)-6-chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinolin-4-amine

HRID 540127Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 540127
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[S:15](=[O:24])(=[O:23])[CH2:14][CH2:13]1)[CH:6]=[C:5]2[NH:25][CH:26]1[CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]1.Cl>O1CCOCC1>[NH:28]1[CH2:29][CH:26]([NH:25][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=3)[N:8]=[C:7]([N:12]3[CH2:18][C:17]4[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=4[S:15](=[O:23])(=[O:24])[CH2:14][CH2:13]3)[CH:6]=2)[CH2:27]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 71255331tert-Butyl 3-[6-chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-quinolin-4-ylamino]-azetidine-1-carboxylate

Produkt 1

HCID 71255852N-(Azetidin-3-yl)-6-chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinolin-4-amineAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 3-[6-chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-quinolin-4-ylamino]-azetidine-1-carboxylate (120 mg, 0.2 mmol) and a solution of hydrochloride in 1,4-dioxane (4 N, 20 mL) was stirred at room temperature for 16 hours. The resulting mixture was concentrated in vacuo. The residue was purified by preparative HPLC to afford 50 mg of the desired product (yield was 51%). MS obsd. (ESI+) [(M+H)+] 429, 1H NMR (400 MHz, CD3OD) δ ppm 8.31 (s, 1 H), 8.08-8.06 (d, J=8 Hz, 1 H), 7.87-7.80 (m, 2 H), 7.73-7.68 (m, 2 H), 7.55-7.53 (m, 1 H), 5.84 (s, 1 H), 5.30 (s, 2 H), 4.99-4.96 (m, 1 H), 4.59-4.52 (m, 4 H), 4.32-4.27 (m, 2 H), 3.72 (s, 2 H).

Aufarbeitung

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. customThe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ff16e960d6b24460bc5dd5f822e32f83
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871756B2

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