Methanesulfonyl chloride → 2-{7-[(3,4-Difluorophenyl)methoxy]-1,5-naphthyridin-3-yl}acetonitrile

HRID 1748412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748412
CS(O[CH2:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[N:14][CH:13]=[C:12]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=1)[CH:11]=2)(=O)=O.FC1C=C(C=CC=1F)COC1C=C2C(C=C(CO)C=N2)=[N:35][CH:34]=1.CS(Cl)(=O)=O>C(Cl)Cl>[F:26][C:21]1[CH:20]=[C:19]([CH2:18][O:17][C:12]2[CH:11]=[C:10]3[C:15]([CH:16]=[C:7]([CH2:6][C:34]#[N:35])[CH:8]=[N:9]3)=[N:14][CH:13]=2)[CH:24]=[CH:23][C:22]=1[F:25]

Komponenten

5

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 86301659(7-((3,4-Difluorobenzyl)oxy)-1,5-naphthyridin-3-yl)methanolHCID 90418375(7-((3,4-Difluorobenzyl)oxy)-1,5-naphthyridin-3-yl)methyl methanesulfonate

Produkt 1

HCID 863016602-{7-[(3,4-Difluorophenyl)methoxy]-1,5-naphthyridin-3-yl}acetonitrileAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(7-((3,4-difluorobenzyl)oxy)-1,5-naphthyridin-3-yl)methyl methanesulfonate. To a solution of (7-((3,4-difluorobenzyl)oxy)-1,5-naphthyridin-3-yl)methanol (Example 73, 90 mg, 0.3 mmol) in DCM (4 mL) was added methanesulfonyl chloride (0.05 mL, 0.61 mmol) followed by TEA (0.06 mL, 0.43 mmol). The reaction mixture was stirred at RT for 1 h and quenched with saturated NaHCO3 solution. The mixture was extracted with DCM (2×) and the combined organic layers were dried, filtered and concentrated under reduced pressure. Purification (FCC, SiO2, 0-80%, EtOAc/hexanes) afforded the title compound as a white solid (73 mg, 64%). [M+H]=381.1.

Aufarbeitung

  1. customquenched with saturated NaHCO3 solution
  2. extractionThe mixture was extracted with DCM (2×)
  3. customthe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification (FCC, SiO2, 0-80%, EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8d7cd42cd04b41eb8847ef2ddfc9f335
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150572B2

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