1-chloro-N-(2-chloro-4-fluoro-5-isocyanatophenyl)methanesulfonamide → 1-chloro-N-[2-chloro-4-fluoro-5-(hexahydro-7-hydroxy-1,3-dioxoimidazo[1,5-a]pyridin-2(3H)-yl)phenyl]methanesulfonamide

HRID 1107256

Reaktionsgleichung

Reaktionsgleichung von HRID 1107256
[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[C:11]([N:13]=[C:14]=[O:15])[C:10]([F:16])=[CH:9][C:8]=1[Cl:17])(=[O:5])=[O:4].[OH:18][C@H:19]1[CH2:24][CH2:23][NH:22][C@@H:21]([C:25](OC)=[O:26])[CH2:20]1>ClCCl>[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[C:11]([N:13]2[C:25](=[O:26])[CH:21]3[CH2:20][CH:19]([OH:18])[CH2:24][CH2:23][N:22]3[C:14]2=[O:15])[C:10]([F:16])=[CH:9][C:8]=1[Cl:17])(=[O:4])=[O:5]

Komponenten

4

Edukt 2

HCID 110774021-chloro-N-(2-chloro-4-fluoro-5-isocyanatophenyl)methanesulfonamideHCID 11321108methyl (2R,4S)-4-hydroxypiperidine-2-carboxylate

Produkt 1

HCID 187868841-chloro-N-[2-chloro-4-fluoro-5-(hexahydro-7-hydroxy-1,3-dioxoimidazo[1,5-a]pyridin-2(3H)-yl)phenyl]methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of the title compound of Example 1, Step E (4.54 g, 15.2 mmol) in dichloromethane (20 mL) was added dropwise a solution of methyl cis-4-hydroxy-2-piperidinecarboxylate (2.41 g, 15.2 mmol, prepared as described in J. Org. Chem. (1991), 4084) in dichloromethane (20 mL) at room temperature. The reaction was stirred at room temperature for 20 hours, quenched by the addition of water, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water and dried over magnesium sulfate. The solvent was removed under reduced pressure and the title compound of Step A, a compound of this invention, was isolated as a foam by flash chromatography (4.98 g). 1H NMR (Me2SO-d6) δ 10.1 (br s, 1H), 7.75 (m, 1H), 7.4 (dd, 1H), 5.1 (m, 1H), 4.9 (s, 2H), 4.1-3.9 (m, 3H), 3.75 (m, 1H), 2.95 (m, 1H), 2.05 (m, 1H), 1.9 (br d, 1H), 1.2 (m, 1H).

Aufarbeitung

  1. customquenched by the addition of water
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-be68f129a4b0472e8a63f49890fa324a
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06060432

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