Triethylamine → (R)-1-[4-(1-Methyl-3-oxo-2-quinoxalin-2-yl-1,2,3,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-5-yl)-pyrimidin-2-yl]-ethyl butyrate

HRID 2227813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2227813
Cl.[CH3:2][N:3]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[C:5](=[O:12])[N:4]1[C:13]1[CH:22]=[N:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1.[C:23]([O:28][C@@H:29]([C:31]1[N:36]=[C:35](Cl)[CH:34]=[CH:33][N:32]=1)[CH3:30])(=[O:27])[CH2:24][CH2:25][CH3:26].C(N(CC)CC)C>C(O)(C)C>[C:23]([O:28][C@@H:29]([C:31]1[N:32]=[C:33]([N:8]2[CH2:9][CH2:10][C:11]3[N:3]([CH3:2])[N:4]([C:13]4[CH:22]=[N:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]=4)[C:5](=[O:12])[C:6]=3[CH2:7]2)[CH:34]=[CH:35][N:36]=1)[CH3:30])(=[O:27])[CH2:24][CH2:25][CH3:26]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10944226(R)-1-(4-chloro-pyrimidin-2-yl)ethyl butyrateHCID 223287161-Methyl-2-quinoxalin-2-yl-1,2,4,5,6,7-hexahydro-pyrazolo[4,3-c]pyridin-3-one hydrochloride

Produkt 1

HCID 20767623(R)-1-[4-(1-Methyl-3-oxo-2-quinoxalin-2-yl-1,2,3,4,6,7-hexahydro-pyrazolo[4,3-c]pyridin-5-yl)-pyrimidin-2-yl]-ethyl butyrateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-methyl-2-quinoxalin-2-yl-1,2,4,5,6,7-hexahydro-pyrazolo[4,3-c]pyridin-3-one hydrochloride (prepared according to the method of Example 75, Step C, 175 mg, 0.55 mmol) and (R)-1-(4-chloro-pyrimidin-2-yl)-ethyl butyrate (prepared according to the method of Preparation Seven, 126 mg, 0.55 mmol) in isopropanol (6 mL) was added triethylamine (230 μL, 1.66 mmol). This mixture was heated to reflux overnight, cooled to room temperature, and evaporated. The residue was diluted with saturated aqueous sodium bicarbonate and extracted with chloroform (3×). The combined organic extracts were dried over sodium sulfate, filtered, evaporated, and purified by flash column chromatography (1.5% methanol/chloroform) to give 248 mg (95%) of the title compound of Example 75, Step D as a yellow oil. 1H NMR (CDCl3, 250 MHz) δ9.70 (s, 1H), 8.29 (d, 1H), 8.15 (dd, 1H), 8.03 (m, 1H), 7.82-7.70 (c, 2H), 6.48 (d, 1H) 5.72 (q, 1H), 4.36 (s, 2H), 4.35-4.15 (c, 2H), 3.42 (s, 3H), 2.77-2.82 (c, 2H), 2.43 (t, 2H), 1.79-1.60 (c, 2H), 1.61 (d, 3H), 0.99 (t, 3H); MS (APCI) 474 (MH+).

Aufarbeitung

  1. customprepared
  2. temperatureThis mixture was heated
  3. temperatureto reflux overnight
  4. customevaporated
  5. additionThe residue was diluted with saturated aqueous sodium bicarbonate
  6. extractionextracted with chloroform (3×)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. custompurified by flash column chromatography (1.5% methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-701c44bbe12d4cf4acb3e7a0ab03a7d2
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06414149B1

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