Hydrochloric Acid → HCID 86723915、化合物

HRID 576813ノート

反応式

HRID 576813 の反応式
C[O:2][CH:3]=[CH:4][C@H:5]([N:7]1[C:12](=[O:13])[C:11]([C:14]2[N:18]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)[N:17]=[CH:16][CH:15]=2)=[C:10]([CH3:27])[N:9]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[C:8]1=[O:38])[CH3:6].Cl.O.C(OCC)(=O)C>O1CCCC1>[CH3:27][C:10]1[N:9]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[C:8](=[O:38])[N:7]([C@@H:5]([CH2:4][CH:3]=[O:2])[CH3:6])[C:12](=[O:13])[C:11]=1[C:14]1[N:18]([C:19]2[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)[N:17]=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 86723914HCID 86723914、化合物

生成物 1

HCID 86723915HCID 86723915、化合物収率 105.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of (R)-4-(5-(3-(4-methoxy-3-buten-2-yl)-6-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (prepared in Example 397) (300 mg) in tetrahydrofuran (3.0 ml) was added 1N hydrochloric acid (10 ml) and the resulting mixture was stirred at 50° C. for two hours. To the reaction mixture was added water (10 ml) followed by an addition of ethyl acetate (20 ml×2) such that the intended products were extracted into an organic layer. The organic layer was washed with saturated saline (10 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford (R)-4-(5-(6-methyl-2,4-dioxo-3-(4-oxobutane-2-yl)-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (309 mg). UPLC/MS 508 (M+H)/1.06 min (measurement condition 9)

後処理

  1. extractionwere extracted into an organic layer
  2. washThe organic layer was washed with saturated saline (10 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-4d75ce34427749dcacc9bb19c5727c43
出典データセット
uspto-grants-2015_05
特許番号
US09040516B2

反応ノート

読み込み中…