反応式
[S:1]1[CH:5]=[C:4]([CH2:6][OH:7])[N:3]=[CH:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH:18]1([NH:21][C:22]([C:24]2[CH:25]=[CH:26][C:27]([CH3:43])=[C:28]([NH:30][C:31]([C:33]3[CH:34]=[N:35][C:36](S(C)(=O)=O)=[N:37][CH:38]=3)=[O:32])[CH:29]=2)=[O:23])[CH2:20][CH2:19]1>C1COCC1>[CH:18]1([NH:21][C:22]([C:24]2[CH:25]=[CH:26][C:27]([CH3:43])=[C:28]([NH:30][C:31]([C:33]3[CH:34]=[N:35][C:36]([O:7][CH2:6][C:4]4[N:3]=[CH:2][S:1][CH:5]=4)=[N:37][CH:38]=3)=[O:32])[CH:29]=2)=[O:23])[CH2:20][CH2:19]1参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
実験手順
To a solution of thiazole-4-methanol (79 mg) in THF (1 mL) at 0° C. under argon was added 1M lithium bis(trimethylsilyl)amide in THF (0.35 mL). After 30 minutes N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-(methylsulfonyl)pyrimidine-5-carboxamide (127 mg, 0.34 mmol) in THF (3 mL) was added and the reaction warmed to room temperature and stirred for 5 hours. The reaction mixture was partitioned between ethyl acetate and water, the organic phases washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on a 12 g silica cartridge eluting with a gradient of 0 to 5% Methanol/DCM to give the title compound as a solid (31 mg, 23%); NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 2.29 (s, 3H), 2.85 (m, 1H), 5.63 (s, 2H), 7.36, (d, 1H) 7.67 (dd, 1H), 7.83 (dd, 2H), 8.49 (d, 1H), 9.14 (m, 2H), 10.14 (s, 1H); Mass Spectrum: M+H+ 410.
後処理
- customThe reaction mixture was partitioned between ethyl acetate and water
- washthe organic phases washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe residue was purified by flash chromatography on a 12 g silica cartridge
- washeluting with a gradient of 0 to 5% Methanol/DCM
出典と根拠
- ORDレコード
- ord-e2884078bb1e41baa59ef7bdf317b1ac
- 出典データセット
- uspto-grants-2014_06
- 特許番号
- US08742124B2
関連ノート
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