Diisopropylethylamine → {6-Fluoro-4-[1-(pyridine-2-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester

HRID 2363829노트

반응식

HRID 2363829 반응식
C(N(C(C)C)CC)(C)C.FC(F)(F)C(O)=O.[CH3:17][O:18][C:19](=[O:38])[CH2:20][C:21]1[CH:30]=[C:29]([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([F:37])[CH:27]=2)[CH:22]=1.[N:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[S:45](Cl)(=[O:47])=[O:46]>C(Cl)Cl>[CH3:17][O:18][C:19](=[O:38])[CH2:20][C:21]1[CH:30]=[C:29]([CH:31]2[CH2:36][CH2:35][N:34]([S:45]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][N:39]=3)(=[O:47])=[O:46])[CH2:33][CH2:32]2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([F:37])[CH:27]=2)[CH:22]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 86686887HCID 86686887, 화합물

생성물 1

HCID 86686894{6-Fluoro-4-[1-(pyridine-2-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester수율 30.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Diisopropylethylamine (0.4 mL, 2.3 mmol) was added at 0° C. to a solution of (6-fluoro-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester trifluoroacetate salt (which may be prepared as described above; 100 mg, 0.24 mmol) in CH2Cl2 (6 mL). The solution was stirred at room temperature for 30 min and then a solution of pyridine-2-sulfonyl chloride (which may be prepared as described above; 213 mg, 1.2 mmol) in CH2Cl2 (1 mL) was added. The mixture was stirred at room temperature for 16 h. The solvent was evaporated under reduced pressure The residue was purified by chromatography on silica gel using a Biotage purification system, eluting with 25% ethyl acetate/hexanes, to give {6-fluoro-4-[1-(pyridine-2-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (32 mg, 30%) as a white solid. MS cald. for C23H24FN2O4S [(M+H)+]: 443, obsd. 443.3.

후처리

  1. stirringThe mixture was stirred at room temperature for 16 h
  2. customThe solvent was evaporated under reduced pressure The residue
  3. customwas purified by chromatography on silica gel using
  4. customa Biotage purification system
  5. washeluting with 25% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-f90a9dc1addf4e028af6bc4e73e354f6
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691993B2

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