Pyridine → HCID 58577920, Verbindung

HRID 473963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 473963
[CH2:1]([CH:3]1[O:8][C:7]2[CH:9]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23])=[N:17][CH:18]=3)[CH:11]=[CH:12][C:6]=2[NH:5][CH2:4]1)[CH3:2].N1C=CC=CC=1.[Cl:34][C:35](Cl)([O:37]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Cl:34][C:35]([N:5]1[CH2:4][CH:3]([CH2:1][CH3:2])[O:8][C:7]2[CH:9]=[C:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]([CH3:26])([CH3:27])[C:22]([O:24][CH3:25])=[O:23])=[N:17][CH:18]=3)[CH:11]=[CH:12][C:6]1=2)=[O:37]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 58577961HCID 58577961, Verbindung

Produkt 1

HCID 58577920HCID 58577920, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of methyl 3-(5-(2-ethyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)pyridin-2-yloxy)-2,2-dimethylpropanoate B-10 (248.0 mg, 0.60 mmol) and dry pyridine (97.0 μL, 1.20 mmol) in anhydrous methylene chloride (3.0 mL) was added dropwise to a solution of triphosgene (71.2 mg, 0.24 mmol) in anhydrous methylene chloride (3.0 mL) at −20° C. under an atmosphere of argon. The reaction mixture was allowed to warm to room temperature over 30 mins and was stirred for 3 h at room temperature. It was then successively diluted with methylene chloride (25 mL), quenched with a 1 N aqueous solution of hydrogen chloride (1.0 mL), diluted with water (10 mL) and decanted. The aqueous layer was extracted with methylene chloride (3×30 mL); the combined extracts were washed with a 1 N aqueous solution of hydrogen chloride (20 mL), brine (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The light pink solid methyl 3-(5-(4-(chlorocarbonyl)-2-ethyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)pyridin-2-yloxy)-2,2-dimethylpropanoate B-11 (265.0 mg, Yield=100%) was used for the next step without purification and stored at −20° C. under an atmosphere of nitrogen. MS (ESI) [M+1]+ 433.

Aufarbeitung

  1. customquenched with a 1 N aqueous solution of hydrogen chloride (1.0 mL)
  2. additiondiluted with water (10 mL)
  3. customdecanted
  4. extractionThe aqueous layer was extracted with methylene chloride (3×30 mL)
  5. washthe combined extracts were washed with a 1 N aqueous solution of hydrogen chloride (20 mL), brine (20 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe light pink solid methyl 3-(5-(4-(chlorocarbonyl)-2-ethyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)pyridin-2-yloxy)-2,2-dimethylpropanoate B-11 (265.0 mg, Yield=100%) was used for the next step without purification
  10. customstored at −20° C. under an atmosphere of nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-776e0cd33417430b949b6e2a6ed3c841
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637507B2

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