Acetic Acid → HCID 178496565, Verbindung

HRID 1890844

Reaktionsgleichung

Reaktionsgleichung von HRID 1890844
C[N:2](/[CH:4]=[N:5]\[C:6](=O)[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:15]=[N:16][C:17]3[NH:22][CH2:21][C:20](=[O:23])[N:19]([CH2:24][C@H:25]4[CH2:30][CH2:29][C@H:28]([O:31][CH3:32])[CH2:27][CH2:26]4)[C:18]=3[N:33]=2)=[CH:9][N:8]=1)C.C(O)(=O)C.[NH2:39]N>O>[CH3:32][O:31][C@H:28]1[CH2:29][CH2:30][C@H:25]([CH2:24][N:19]2[C:18]3=[N:33][C:14]([C:10]4[CH:9]=[N:8][C:7]([C:6]5[N:5]=[CH:4][NH:2][N:39]=5)=[CH:12][C:11]=4[CH3:13])=[CH:15][N:16]=[C:17]3[NH:22][CH2:21][C:20]2=[O:23])[CH2:26][CH2:27]1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 178496568HCID 178496568, Verbindung

Produkt 1

HCID 178496565HCID 178496565, VerbindungAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(Z)—N-((Dimethylamino)methylene)-5-(8-(((trans)-4-methoxycyclohexyl)methyl)-7-oxo-5,6,7,8-tetrahydropyrazino[2,3-b]pyrazin-2-yl)-4-methylpicolinamide (0.467 g, 1.00 mmol) was added to acetic acid (6 mL). The reaction was cooled to 0° C. and hydrazine (1.00 mL, 32 mmol) was added dropwise. The reaction was allowed to stir and warm to 25° C. over 10 min. Reaction was concentrated under a stream of nitrogen placed in reaction vessel. Water (5 mL) was added and the product was collected by filtration and purified using reverse-phase semi-preparatory HPLC (20-70% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min). Clean fractions were combined and condensed under reduced pressure and dried under high vacuum to afford the title compound as a yellow solid (0.046 g, 0.106 mmol, 11% yield). 1H NMR (400 MHz, METHANOL-d4) δ (ppm) 8.72 (s, 1H), 8.62 (s, 1H), 8.37 (s, 1H), 7.93 (s, 1H), 4.30 (s, 2H), 3.99 (d, J=7.03 Hz, 2H), 3.32 (s, 3H), 3.08-3.17 (m, 1H), 2.71-2.76 (m, 3H), 2.06 (br. s., 2H), 1.80-1.89 (m, 1H), 1.74 (br. s., 2H), 1.09 (d, J=11.32 Hz, 4H); MS (ESI) m/z 435.5 [M+1]+.

Aufarbeitung

  1. temperaturewarm to 25° C. over 10 min
  2. customReaction
  3. concentrationwas concentrated under a stream of nitrogen
  4. customplaced in reaction vessel
  5. filtrationthe product was collected by filtration
  6. custompurified
  7. customreverse-phase semi-preparatory HPLC (20-70% acetonitrile+0.1% TFA in H2O+0.1% TFA, over 30 min)
  8. customcondensed under reduced pressure
  9. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3ee6ed9033b94a6e8b3480953cb595fd
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507492B2

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