Diethyl Sulfate → (6S-cis)-1-chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)phenyl]-N-ethylmethanesulfonamide

HRID 1107254노트

반응식

HRID 1107254 반응식
[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[C:11]([N:13]2[C:17](=[O:18])[C@H:16]3[CH2:19][C@H:20]([F:22])[CH2:21][N:15]3[C:14]2=[O:23])[C:10]([F:24])=[CH:9][C:8]=1[Cl:25])(=[O:5])=[O:4].[CH2:26](OS(OCC)(=O)=O)[CH3:27].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][CH2:2][S:3]([N:6]([C:7]1[CH:12]=[C:11]([N:13]2[C:17](=[O:18])[C@H:16]3[CH2:19][C@H:20]([F:22])[CH2:21][N:15]3[C:14]2=[O:23])[C:10]([F:24])=[CH:9][C:8]=1[Cl:25])[CH2:26][CH3:27])(=[O:5])=[O:4]

참가 물질

5

반응물 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 11037075Profluazol

생성물 1

HCID 21968480(6S-cis)-1-chloro-N-[2-chloro-4-fluoro-5-(6-fluorotetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)phenyl]-N-ethylmethanesulfonamide

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of the title compound of Example 1, Step H (0.414 g, 1 mmol), diethylsulfate (0.17 g, 1.1 mmol), and potassium carbonate (0.27 g) in acetone (10 mL) was stirred at room temperature for 4 h. After completion of the reaction, the potassium carbonate was filtered off and the solvent was removed on a rotary evaporator. The title compound of Step A, a compound of this invention, was isolated by flash chromatography (0.41 g, 92%) as a white solid melting at 198-200° C. 1H NMR (CDCl3) δ 7.46 (d, 1H), 7.42 (d, 1H), 5.52 (m, 1H), 4.62 (dd, 1H), 4.59 (s, 2H), 4.02 (dd, 1H), 3.80 (m, 4H), 3.60 (dd, 1H), 2.64 (m, 1H), 2.01 (m, 1H), 1.20 (t, 6).

후처리

  1. customAfter completion of the reaction
  2. filtrationthe potassium carbonate was filtered off
  3. customthe solvent was removed on a rotary evaporator

출처 및 근거

ORD 기록
ord-be27adc720f04e0bbba5dab2d26953b0
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06060432

반응 노트

불러오는 중…