Water → HCID 178504697, 화합물

HRID 2231114노트

반응식

HRID 2231114 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([SH:23])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Cl.Cl[CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1.C(N(CC)CC)C.O>CC(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([S:23][CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 178504698HCID 178504698, 화합물

생성물 1

HCID 178504697HCID 178504697, 화합물수율 95.8%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A solution of 4-(4-fluorophenyl)-5-(4-(methylsulfonyl)phenyl]-1H-imidazole-2-thiol (Example 49) (100 mg, 0.29 mmol), 2-chloromethylquinoline hydrochloride (62 mg, 0.29 mmol) and triethylamine (60 mg, 0.58 mmol) in 2-propanol (5 ml) was heated at reflux under an argon atmosphere for 4 hours. The reaction was cooled, poured into water (25 ml) and extracted with ethyl acetate. After drying over sodium sulfate, the solvent was removed and the residue was purified by chromatography on silica gel using 50% ethyl acetate in toluene as the eluent to give 136 mg (85%) of the desired product. Although initially an oil, this material crystallized on standing: mp 179-182° C. Anal. Calc'd. for C26H20N3O2FS2.5H2O (MW 498.60): C, 62.63; H, 4.25; N, 8.43; S, 12.86. Found: C, 62.98; H, 4.43; N, 8.03; S, 12.60.

후처리

  1. temperatureat reflux under an argon atmosphere for 4 hours
  2. temperatureThe reaction was cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialAfter drying over sodium sulfate
  5. customthe solvent was removed
  6. customthe residue was purified by chromatography on silica gel using 50% ethyl acetate in toluene as the eluent

출처 및 근거

ORD 기록
ord-e381a479f0f648768ecd9b2a98928430
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06426360B1

반응 노트

불러오는 중…