反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[NH:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)(O)[O-].[Na+].Br[CH2:26][C:27](=[O:32])[C:28]([F:31])([F:30])[F:29]>C(O)(C)C>[OH:32][C:27]1([C:28]([F:31])([F:30])[F:29])[CH2:26][N:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=2)[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[N:13]1参加物
実験手順
To a mixture of the amidine of step 1 (4.4 g, 16 mmol) and sodium bicarbonate (2.7 g, 32 mmol) in isopropanol (400 ml), 3-bromo-1,1,1-trifluoroacetone (2.5 ml, 24 mmol) was added. After heating at 75–80° C. for 24 hours, the reaction mixture was cooled and filtered. The residue was washed with methylene chloride and the combined organic fractions were dried over sodium sulfate, filtered and concentrated. The crude product (16.2 g) was purified by chromatography (silica gel, ethyl acetate/toluene 1/1) to give 2-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine (1.1 g, 18%) as a white solid: mp 195–198° C. Anal. Calc'd. for C16H14N3SO3F3: C, 49.87; H, 3.66; N, 10.90. Found: C, 50.13; H, 3.66; N, 10.30.
後処理
- additionwas added
- temperatureAfter heating at 75–80° C. for 24 hours
- temperaturethe reaction mixture was cooled
- filtrationfiltered
- washThe residue was washed with methylene chloride
- dry with materialthe combined organic fractions were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product (16.2 g) was purified by chromatography (silica gel, ethyl acetate/toluene 1/1)
出典と根拠
- ORDレコード
- ord-6eb382aa29f548549edf79ce99cf12d1
- 出典データセット
- uspto-grants-2007_05
- 特許番号
- US07220770B2
関連ノート
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