Dimethyl Sulfoxide → 4-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

HRID 20640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20640
[H-].[Na+].[NH2:3][C:4]1[C:13]2[C:8](=[C:9]([O:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[O:7][C:6](=[O:22])[CH:5]=1.CS(C)=O.[Br:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([Cl:35])[C:33]=1Cl>[Cl-].[Na+].O>[Br:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([Cl:35])[C:33]=1[NH:3][C:4]1[C:13]2[C:8](=[C:9]([O:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[O:7][C:6](=[O:22])[CH:5]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 687426533-Bromo-4,5-dichloropyridineHCID 771747934-amino-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

Produkt 1

HCID 248494324-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Sodium hydride (7 mg, 60%, 0.18 mmol) was added to a solution of 4-amino-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (77 mg, 0.28 mmol, Example 3, Step 1) and anhydrous DMSO (3 mL) under N2. After 10 min, 3-bromo-4,5-dichloropyridine (69 mg, 0.31 mmol) was added, and the reaction was stirred for 20 h, poured into brine, and extracted with EtOAc. The organic extract was dried, filtered, concentrated, and purified by reverse-phase HPLC (20→100% MeCN/H2O) to give 4-(3-bromo-5-chloropyridin-4-ylamino)-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one: 1H NMR (400 MHz, DMSO-d6): δ 9.54 (s, 1H), 8.91 (s, 1H), 8.84 (s, 1H), 7.95 (d, 1H), 7.21 (d, 1H), 4.85 (m, 1H), 4.59 (s, 1H), 3.92 (s, 3H), 1.87-1.79 (m, 4H), 1.68-1.54 (m, 4H); MS (ESI): 464.7.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. customwas dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by reverse-phase HPLC (20→100% MeCN/H2O)

Quellen und Nachweise

ORD-Eintrag
ord-dccd032796f642beb0e66a4b9d608b32
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745646B2

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