N-Aminomorpholine → HCID 66740466、化合物

HRID 1627279ノート

反応式

HRID 1627279 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([S:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][C:28]([S:32]([NH:35][C:36](=[O:40])OCC)(=[O:34])=[O:33])=[CH:27][C:26]=3[F:41])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:42][CH3:43].[NH2:44][N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[C:14]([S:23][CH2:24][C:25]3[C:26]([F:41])=[CH:27][C:28]([S:32]([NH:35][C:36](=[O:40])[NH:44][N:45]4[CH2:50][CH2:49][O:48][CH2:47][CH2:46]4)(=[O:34])=[O:33])=[CH:29][C:30]=3[F:31])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:42][CH3:43]

参加物

5

反応物 2

HCID 20315N-AminomorpholineHCID 66739854Ethyl 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonylcarbamate

生成物 1

HCID 66740466HCID 66740466、化合物収率 46.9%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Ethyl 4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenylsulfonylcarbamate (76 mg, 0.12 mmol, 1.0 eq) and 4-aminomorpholine (0.045 mL, 0.46 mmol, 4.0 eq) in toluene (2.5 mL, anhyd) were heated at reflux for 2.5 h. The reaction mixture was cooled to room temperature, diluted with EtOAc and washed with water, followed by brine. After drying (MgSO4), the organics were concentrated and purified by chromatography (silica, 0 to 80% EtOAc/Hex, then 10% MeOH/DCM) to provide the title compound (40 mg). 1H NMR (400 MHz, DMSO-d6) δ 8.33 (s, 1H), 7.41-7.16 (m, 4H), 7.03-6.90 (m, 3H), 6.57-6.43 (m, 4H), 4.02-3.98 (m, 2H), 3.71-3.65 (m, 3H), 3.57-3.50 (m, 3H), 3.48-3.38 (m, 1H), 3.31-3.25 (m, 1H), 2.69-2.58 (m, 3H), 1.46 (s, 6H); MS (EI) m/z 710.1 (MH+).

後処理

  1. temperatureat reflux for 2.5 h
  2. washwashed with water
  3. dry with materialAfter drying (MgSO4)
  4. concentrationthe organics were concentrated
  5. custompurified by chromatography (silica, 0 to 80% EtOAc/Hex

出典と根拠

ORDレコード
ord-81b4184b03ee480ca010d837eeca4a6e
出典データセット
uspto-grants-2014_07
特許番号
US08785488B2

反応ノート

読み込み中…