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Hydrochloric Acid → 7-(2-m-Tolyl-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

HRID 406192
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 406192
[C:1]1([CH3:35])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:2]=1.CO.[OH-].[Na+].Cl>C1COCC1.O>[C:1]1([CH3:35])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:10]3=[N:11][C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)[CH:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 66665344Ethyl 7-(2-m-tolyl-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Produkt 1

HCID 566442747-(2-m-Tolyl-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
2×
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethyl 7-(2-m-tolyl-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 1)(69 mg, 0.146 mmol) in THF (1 ml) and water (0.5 ml) at RT was treated with LiOH monohydrate (18.42 mg, 0.439 mmol) and stirred at RT for 4 hours. MeOH (1 ml) and 2M NaOH (1 ml) were added and the mixture was stirred at RT overnight. The resulting mixture was added to water (20 ml) and the pH was adjusted to pH1 with 2M HCl. The aqueous portion was extracted with DCM (×3) and the organic extracts were passed through a phase separating column. The organic solvent was concentrated in vacuo. The crude product was purified by preparative LC-MS (low pH). The appropriate fraction was collected and extracted with DCM (×3), passing the organics through a phase separating column. The solvent was removed in vacuo to afford the title compound;

Aufarbeitung

  1. stirringthe mixture was stirred at RT overnight
  2. extractionThe aqueous portion was extracted with DCM (×3)
  3. customseparating column
  4. concentrationThe organic solvent was concentrated in vacuo
  5. customThe crude product was purified by preparative LC-MS (low pH)
  6. customThe appropriate fraction was collected
  7. extractionextracted with DCM (×3)
  8. customseparating column
  9. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d166124aff6f4465b0a723dc331183be
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08754085B2

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