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Lithium Hydroxide → 5-(5-Phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinic acid

HRID 593706
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 593706
[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[N:10][N:11]=[C:12]3[C:17]2[CH:18]=[N:19][CH:20]=[C:21]([CH:27]=2)[C:22]([O:24]CC)=[O:23])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-]>CCO.C1COCC1.O>[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[N:10][N:11]=[C:12]3[C:17]2[CH:18]=[N:19][CH:20]=[C:21]([CH:27]=2)[C:22]([OH:24])=[O:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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Komponenten

6

Edukt 2

HCID 3939Lithium HydroxideHCID 90424789Ethyl 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinate

Produkt 1

HCID 904238795-(5-Phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinic acidAusbeute 13,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinate (0.120 g, 0.260 mmol) in EtOH (6 mL) and THF (6 mL) was added LiOH (0.0620 g, 2.60 mmol) in water (3 mL) at room temperature. The reaction mixture was stirred at the same temperature for 16 h. Then the reaction mixture was concentrated under reduced pressure and the resulting residue was diluted with water (5 mL). The reaction mixture was extracted with EtOAc and the aqueous layer was separated. The aqueous layer was acidified to pH 5 with citric acid and extracted with EtOAc. The organic extract was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by HPLC (Condition 13 as described in general methods) to afford 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinic acid (0.0150 g, 13.3%). LCMS (Condition 2): retention time 1.54 min, [M-1]=432.0. HPLC (Condition 25): retention time=5.86 min, purity 95.51%. 1H NMR (400 MHz, DMSO-d6) δ 4.66 (d, J=4.4 Hz, 2 H), 6.25 (dd, J=4.0 Hz, J=4.4 Hz, 1 H), 7.20-7.24 (m, 1 H), 7.28 (d, J=7.6 Hz, 1 H), 7.52-7.59 (m, 5 H), 7.68-7.73 (m, 2 H), 7.82 (dd, J=1.2 Hz, J=8.4 Hz, 1 H), 7.91 (dd, J=7.2 Hz, J=8.4 Hz, 1 H), 8.22-8.25 (m, 1 H), 8.35 (dd, J=1.6 Hz, J=2.0 Hz, 1 H), 8.74 (d, J=2.0 Hz, 1 H), 9.09 (d, J=1.6 Hz, 1 H).

Aufarbeitung

  1. concentrationThen the reaction mixture was concentrated under reduced pressure
  2. additionthe resulting residue was diluted with water (5 mL)
  3. extractionThe reaction mixture was extracted with EtOAc
  4. customthe aqueous layer was separated
  5. extractionextracted with EtOAc
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by HPLC (Condition 13 as described in general methods)

Quellen und Nachweise

ORD-Eintrag
ord-e22146a128c84ee491c1b937b7e9e863
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242966B2

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