Pyridine → 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5-dicyano-3-propyl-1,3-dihydro-2H-imidazol-2-one

HRID 465692노트

반응식

HRID 465692 반응식
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:13]([C:14]#[N:15])=[C:12]([C:16]#[N:17])[N:11]([CH3:18])[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1.C(O[C:25](=O)[CH3:26])(=O)C.N1C=C[CH:31]=[CH:30][CH:29]=1>>[Cl:1][C:2]1[C:7]([O:8][CH2:31][C:30]#[CH:29])=[CH:6][C:5]([N:9]2[C:13]([C:14]#[N:15])=[C:12]([C:16]#[N:17])[N:11]([CH2:18][CH2:25][CH3:26])[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1

참가 물질

4

반응물 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 198751891-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one3회

생성물 1

HCID 198752701-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5-dicyano-3-propyl-1,3-dihydro-2H-imidazol-2-one

실험 절차

The product of Example 32, 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one, (VIII) (200 mg, 0.68 mmol) was stirred in 10 mL pyridine at room temperature. To this mixture was added acetic anhydride (100 mg, 0.98 mmol). After stirring for 10 minutes the mixture was poured over a mixture of ice/HCl and filtered. Recrystallization from ethyl acetate/heptane gave 60 mg of 1-(4-chloro-2-fluoro-5-acetoxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one (VI) (m.p. 164°-6° C.).

후처리

  1. filtrationfiltered
  2. customRecrystallization from ethyl acetate/heptane

출처 및 근거

ORD 기록
ord-00c58af717ab49f6961ef8dbde047771
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153316

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