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Hydrochloric Acid → (E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-3-cyclopropyl-2-(4-hydroxyphenyl)-3-phenylacrylamide

HRID 884067
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HRID 884067 반응식
[CH3:1][N:2]([CH3:36])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:35])/[C:14](/[C:25]2[CH:30]=[CH:29][C:28]([O:31]COC)=[CH:27][CH:26]=2)=[C:15](\[CH:22]2[CH2:24][CH2:23]2)/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8][CH:7]=1.Cl.C([O-])(O)=O.[Na+]>CO.O1CCOCC1.O>[CH3:36][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:35])/[C:14](/[C:25]2[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=2)=[C:15](\[CH:22]2[CH2:24][CH2:23]2)/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:11]=1
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참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68732008(E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-3-cyclopropyl-2-(4-(methoxymethoxy)phenyl)-3-phenylacrylamide

생성물 1

HCID 42603087(E)-N-(4-(2-(dimethylamino)ethoxy)phenyl)-3-cyclopropyl-2-(4-hydroxyphenyl)-3-phenylacrylamide수율 88%

시약·촉매·용매 3

HCID 887
Methanol
용매
HCID 962Water용매
HCID 312751,4-Dioxane용매

실험 절차

To a solution of 8 (70 mg, 0.144 mmol) in MeOH (3 ml) was added 4N HCl in 1,4-dioxane (0.4 ml) under ice cooling, and the mixture was stirred at room temperature for 3 h. A solution of NaHCO3 in H2O was poured into the reaction mixture under ice cooling, and the whole was extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, and then concentrated. The residual solid was crystallized with Et2O to give 9 (88%). 9: colorless powder; 1H-NMR (CD3OD) δ 0.42 (2H, m), 0.73 (2H, m), 1.99 (1H, m), 2.35 (6H, s), 2.77 (2H, t, J=5.4 Hz), 4.10 (2H, t, J=5.4 Hz), 6.47 (2H, d, J=8.8 Hz), 6.91 (2H, d, J=8.8 Hz), 6.94 (2H, d, J=9.1 Hz), 7.06 (2H, m), 7.13-7.23 (3H, m), 7.56 (2H, d, J=9.3 Hz). HRMS calcd for C28H31N2O3 [M+H]+: 443.2335. Found: 443.2353.

후처리

  1. extractionthe whole was extracted with AcOEt
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residual solid was crystallized with Et2O

출처 및 근거

ORD 기록
ord-a51ddd4754e34089823b1e602bf866d8
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08236987B2

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