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

반응식

HRID 1107256 반응식
[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]

참가 물질

4

반응물 2

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

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-be68f129a4b0472e8a63f49890fa324a
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06060432

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