Hydrochloric Acid → HCID 86723915, 화합물

HRID 576813노트

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HRID 576813 반응식
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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 86723914HCID 86723914, 화합물

생성물 1

HCID 86723915HCID 86723915, 화합물수율 105.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-4d75ce34427749dcacc9bb19c5727c43
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040516B2

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