1,4-Dioxane hydrochloride → 1-{4-[2-(1,3-Benzothiazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutanamine trihydrochloride

HRID 1047065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047065
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:11]=[C:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15]3[N:23]=[CH:24][CH:25]=[CH:26][C:14]=3[N:13]2[C:27]=1[C:28]1[CH:33]=[CH:32][C:31]([C:34]2([NH:38]C(=O)OC(C)(C)C)[CH2:37][CH2:36][CH2:35]2)=[CH:30][CH:29]=1.[ClH:46].O1CCOCC1>C(Cl)Cl>[ClH:46].[ClH:46].[ClH:46].[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:11]=[C:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15]3[N:23]=[CH:24][CH:25]=[CH:26][C:14]=3[N:13]2[C:27]=1[C:28]1[CH:29]=[CH:30][C:31]([C:34]2([NH2:38])[CH2:37][CH2:36][CH2:35]2)=[CH:32][CH:33]=1

Komponenten

4

Edukt 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69087701tert-Butyl (1-{4-[2-(1,3-benzothiazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate

Produkt 1

HCID 675034081-{4-[2-(1,3-Benzothiazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutanamine trihydrochlorideAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

tert-Butyl (1-{4-[2-(1,3-benzothiazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (24.8 mg, 0.0405 mmol) was dissolved in DCM (1 mL). 4M HCl/dioxane (1 mL) was added to the mixture and stirred at room temperature for 18 hours. The mixture was concentrated and solidified with ether. The precipitated solids were collected by filtration and washed with ether to afford desired product (21.8 mg, 86.4%) as yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.85-8.65 (m, 3H), 8.16 (dd, J=4.8, 1.6 Hz, 1H), 8.11-8.07 (m, 1H), 7.97 (dd, J=7.8, 1.8 Hz, 1H), 7.83-7.78 (m, 1H), 7.65-7.55 (m, 4H), 7.51-7.46 (m, 1H), 7.45-7.39 (m, 2H), 7.37-7.32 (m, 1H), 7.21-7.15 (m, 1H), 6.98 (dd, J=8.0, 1.6 Hz, 1H), 6.79 (dd, J=8.0, 4.8 Hz, 1H), 2.66-2.54 (m, 4H), 2.28-2.15 (m, 1H), 1.92-1.77 (m, 1H); LCMS: 513 [M+H].

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. filtrationThe precipitated solids were collected by filtration
  3. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-e8fd7f6dbe724a6ab26ce71bf0717f47
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569331B2

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