1,4-Dioxane hydrochloride → Pf-04217903

HRID 16020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 16020
O1CCCCC1[O:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([C:15]2[N:20]=[C:19]3[N:21]([CH2:24][C:25]4[CH:26]=[C:27]5[C:32](=[CH:33][CH:34]=4)[N:31]=[CH:30][CH:29]=[CH:28]5)[N:22]=[N:23][C:18]3=[N:17][CH:16]=2)[CH:12]=[N:11]1.O1CCOCC1.Cl>C(Cl)Cl>[N:31]1[C:32]2[C:27](=[CH:26][C:25]([CH2:24][N:21]3[C:19]4[C:18](=[N:17][CH:16]=[C:15]([C:13]5[CH:12]=[N:11][N:10]([CH2:9][CH2:8][OH:7])[CH:14]=5)[N:20]=4)[N:23]=[N:22]3)=[CH:34][CH:33]=2)[CH:28]=[CH:29][CH:30]=1

Komponenten

4

Edukt 2

HCID 204431481,4-Dioxane hydrochlorideHCID 593417856-(6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl)-quinoline

Produkt 1

HCID 17754438Pf-04217903Ausbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 6-(6-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-pyrazol-4-yl}-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl)-quinoline (780 mg, 1.71 mmol) in CH2Cl2 (20 mL) was added the anhydrous HCl dioxane solution dropwise (4N, 1.07 mL, 4.27 mmol). A white solid was precipitated out. The reaction mixture was stirred for 1 hour and the LCMS showed the completion of the reaction. The reaction mixture was concentrated, and the residue was dissolved in distilled water (15 mL). The solution was adjusted to pH 7 with Na2CO3. An off-white solid was crashed out, which was filtered, washed with water, and dried on a high vacuum for 1 hour. The solid was re-crystallized from EtOH (50 mL) to provide 2-[4-(3-Quinolin-6-ylmethyl-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)-pyrazol-1-yl]-ethanol (400, 63% yield) as a white crystalline solid with a melting point of 222° C. 1H NMR (400 MHz, DMSO-d6) δ 9.22 (s, 1H) 8.89 (dd, J=4.14, 1.70 Hz, 1H) 8.63 (s, 1H) 8.37 (dd, J=8.38, 1.04 Hz, 1H) 8.32 (s, 1H) 7.98-8.04 (m, 2H) 7.82 (dd, J=8.67, 2.07 Hz, 1H) 7.53 (dd, J=8.29, 4.14 Hz, 1H) 6.15 (s, 2H) 4.96 (t, J=5.27 Hz, 1H) 4.24 (t, J=5.46 Hz, 2H) 3.78 (q, J=5.46 Hz, 2H).

Aufarbeitung

  1. customA white solid was precipitated out
  2. customthe completion of the reaction
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in distilled water (15 mL)
  5. filtrationwhich was filtered
  6. washwashed with water
  7. customdried on a high vacuum for 1 hour
  8. customThe solid was re-crystallized from EtOH (50 mL)

Quellen und Nachweise

ORD-Eintrag
ord-b550ff14c42645ee92e730782bb44380
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732604B2

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