Hydrochloric Acid → N-(3-chloro-4-morpholin-4-ylphenyl)-2-[2-(4-methylpiperazin-1-yl)ethyl]-4,5-dihydro-2H-pyrimido[5',4':4,5]thieno[2,3-e]indazol-6-amine

HRID 222018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222018
Cl[C:2]1[C:7]2[C:8]3[CH2:16][CH2:15][C:14]4[C:10](=[CH:11][N:12]([CH2:17][CH2:18][N:19]5[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]5)[N:13]=4)[C:9]=3[S:26][C:6]=2[N:5]=[CH:4][N:3]=1.[Cl:27][C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][C:34]=1[N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1)[NH2:31].Cl.O1CCOCC1>C(O)(C)C>[Cl:27][C:28]1[CH:29]=[C:30]([NH:31][C:2]2[N:3]=[CH:4][N:5]=[C:6]3[S:26][C:9]4[C:10]5[C:14]([CH2:15][CH2:16][C:8]=4[C:7]=23)=[N:13][N:12]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[CH:11]=5)[CH:32]=[CH:33][C:34]=1[N:35]1[CH2:36][CH2:37][O:38][CH2:39][CH2:40]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 1086613-Chloro-4-morpholinoanilineHCID 583466646-chloro-2-[2-(4--methylpiperazin-1-yl)ethyl]-4,5-dihydro-2H-pyrimido[5',4':4,5]thieno[2,3-e]indazole

Produkt 1

HCID 58346454N-(3-chloro-4-morpholin-4-ylphenyl)-2-[2-(4-methylpiperazin-1-yl)ethyl]-4,5-dihydro-2H-pyrimido[5',4':4,5]thieno[2,3-e]indazol-6-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a suspension of 6-chloro-2-[2-(4-methylpiperazin-1-yl)ethyl]-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazole (50 mg, 0.13 mmol) and 3-chloro-4-morpholinoaniline (82 mg, 0.39 mmol) in isopropanol (3 mL) was added HCl in dioxane (4M, 0.26 mL, 1.03 mmol). The reaction mixture was sealed in a microwave reaction vessel and it was placed in a microwave instrument at 160° C. for 10 min. After it was cooled to room temperature, solvents were evaporated and the residue was dissolved in water/DMF and purified by prep. HPLC. After drying, the TFA salt was neutralized with aq saturated NaHCO3 and extracted with a mixture of CHCl3:isopropanol (3:1). The organic phase was dried over Na2SO4 and concentrated to dryness. The desired product was obtained as a pale solid (40 mg, 55%). 1H-NMR (CD2Cl2) δ 8.43 (s, 1H), 7.84 (d, 1H), 7.53 (m, 2H), 7.08 (m, 2H), 4.20 (t, 2H), 3.86 (m, 4H), 3.37 (t, 2H), 3.11 (t, 2H), 3.04 (m, 4H), 2.80 (t, 2H), 2.53 (m, 4H), 2.43 (m, 4H), 2.26 (s, 3H); LCMS RT=2.29 min; [M+H]+=565.4.

Aufarbeitung

  1. customThe reaction mixture was sealed in a microwave reaction vessel and it
  2. customsolvents were evaporated
  3. dissolutionthe residue was dissolved in water/DMF
  4. custompurified by prep
  5. customAfter drying
  6. extractionextracted with a mixture of CHCl3:isopropanol (3:1)
  7. dry with materialThe organic phase was dried over Na2SO4
  8. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-a3e82fe4ccd84e1d8d2686e8e083c5e6
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207172B2

Notizen zur Reaktion

Wird geladen…