反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C(OC(OC(C)C)OC(C)C)(C)C.C1(S(O)(=O)=O)C=CC=CC=1.C(NC(C)C)(C)C.CON(C)[C:43](=[O:63])[C:44]1[CH:49]=[CH:48][C:47]([O:50][C:51]2[C:56]([CH:57]3[CH2:62][CH2:61][S:60][CH2:59][CH2:58]3)=[N:55][CH:54]=[CH:53][N:52]=2)=[CH:46][CH:45]=1.[Li+].CC([N-]C(C)C)C>C1(C)C=CC=CC=1.C1COCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:43]([C:44]1[CH:49]=[CH:48][C:47]([O:50][C:51]2[C:56]([CH:57]3[CH2:62][CH2:61][S:60][CH2:59][CH2:58]3)=[N:55][CH:54]=[CH:53][N:52]=2)=[CH:46][CH:45]=1)=[O:63]参加物
反応物 6
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 0 °C
実験手順
A mixture of 1H-benzo[d]imidazole (0.039 g, 0.334 mmol), triisopropoxymethane (0.529 g, 2.78 mmol), benzenesulfonic acid (2.200 mg, 0.014 mmol) in toluene (5 mL) was heated at reflux for 3 h. The mixture was cooled, neutralized with diisopropylamine (0.1 ml), concentrated to dryness and diluted with 1 ml THF. The above solution was added to a stirred mixture of N-methoxy-N-methyl-4-(3-(tetrahydro-2H-thiopyran-4-yl)pyrazin-2-yloxy)benzamide (0.100 g, 0.278 mmol) in THF (3 mL). The resulting mixture was cooled to 0° C. and LDA (0.167 mL, 0.334 mmol) was added dropwise. The reaction mixture was stirred at RT overnight, quenched with saturated NH4Cl, extracted with EtOAc (3×), dried over MgSO4, concentrated and purified by ISCO (0-5% MeOH/DCM) to give the title compound as a white solid. MS (ESI, pos. ion) m/z: 416.1 (M+1). IC50 (uM) +++++.
後処理
- temperaturewas heated
- temperatureat reflux for 3 h
- temperatureThe mixture was cooled
- concentrationconcentrated to dryness
- additiondiluted with 1 ml THF
- customquenched with saturated NH4Cl
- extractionextracted with EtOAc (3×)
- dry with materialdried over MgSO4
- concentrationconcentrated
- custompurified by ISCO (0-5% MeOH/DCM)
出典と根拠
- ORDレコード
- ord-e5504a42158c47bdb6081aed84d49f75
- 出典データセット
- uspto-grants-2012_08
- 特許番号
- US08247418B2
関連ノート
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