Water → HCID 178504697、化合物

HRID 2231114ノート

反応式

HRID 2231114 の反応式
[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

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 178504698HCID 178504698、化合物

生成物 1

HCID 178504697HCID 178504697、化合物収率 95.8%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e381a479f0f648768ecd9b2a98928430
出典データセット
uspto-grants-2002_07
特許番号
US06426360B1

反応ノート

読み込み中…