Diisopropylethylamine → HCID 66776235, Verbindung

HRID 716300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716300
OC[C:3]1[CH:16]=[N:15][C:6]2[N:7]([CH:12]([CH3:14])[CH3:13])[CH2:8][C:9](=[O:11])[NH:10][C:5]=2[CH:4]=1.[I-].C(C[P+](C)(C)C)#N.C[CH2:26][N:27]([CH:31]([CH3:33])C)[CH:28]([CH3:30])C.Cl.[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2CCNCC=2)=[CH:38][CH:37]=1>C(#N)CC>[Cl:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH2:30][CH2:28][N:27]([CH2:26][N:10]3[C:9](=[O:11])[CH2:8][N:7]([CH:12]([CH3:13])[CH3:14])[C:6]4[N:15]=[CH:16][CH:3]=[CH:4][C:5]3=4)[CH2:31][CH:33]=2)=[CH:38][CH:37]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 27236124-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridinium chlorideHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 583244367-(hydroxymethyl)-4-isopropyl-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

Produkt 1

HCID 66776235HCID 66776235, VerbindungAusbeute 26,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7854PropionitrileLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

7-(hydroxymethyl)-4-isopropyl-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one (100 mg, 0.452 mmol) was taken up as a suspension in propiononitrile (1 mL). Next was added (cyanomethyl)trimethylphosphonium iodide (132 mg, 0.542 mmol) followed by DIPEA (0.237 mL, 1.356 mmol). To the stirred white suspension was then added the 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride (114 mg, 0.50 mmol). The reaction was heated to 90° C. and stirred overnight. The crude reaction was cooled to room temperature and concentrated to a residue, then taken up in 3 mL DMSO and purified via HPLC (55-90% acetonitrile in water, ammonium bicarbonate buffer). The fractions were combined and concentrated until a white solid precipitated. The precipitate was filtered off and dried in vacuum to afford the title compound (46.9 mg, 26%) as a white solid. 1H NMR (DMSO-d6) δ (ppm): 10.50 (s, 1H), 7.65 (d, J=1.8 Hz, 1H), 7.40-7.46 (m, 2H), 7.34-7.39 (m, 2H), 6.98 (d, J=2.0 Hz, 1H), 6.18 (br. s., 1H), 4.76-4.87 (m, 1H), 3.81 (s, 2H), 3.40 (s, 2H), 3.01 (d, J=2.8 Hz, 2H), 2.60 (t, J=5.6 Hz, 2H), 2.43 (br. s., 2H), 1.12 (d, J=6.8 Hz, 6H). [M+H] calc'd for C22H25ClN4O, 397. found, 397.

Aufarbeitung

  1. customThe crude reaction
  2. temperaturewas cooled to room temperature
  3. concentrationconcentrated to a residue
  4. custompurified via HPLC (55-90% acetonitrile in water, ammonium bicarbonate buffer)
  5. concentrationconcentrated until a white solid
  6. customprecipitated
  7. filtrationThe precipitate was filtered off
  8. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0bd307e4cbdc4dd0a601e04bc7c1364f
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09187497B2

Notizen zur Reaktion

Wird geladen…