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Ethyl Acetate → 6-[2-Methoxy-4-(6-methylpyridin-3-ylcarbonyloxy)phenyl]-5-(5-methylthiophen-2-ylcarbonyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 1043679
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HRID 1043679 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH2:21][O:22][C:23]([C:25]3[S:26][C:27]([CH3:30])=[CH:28][CH:29]=3)=[O:24])=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]([CH3:19])([CH3:18])[CH:12]=[C:11]3[CH3:20])=[C:4]([O:31][CH3:32])[CH:3]=1.[CH3:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][N:35]=1.C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CN(C)C=O>[CH3:32][O:31][C:4]1[CH:3]=[C:2]([O:1][C:38]([C:37]2[CH:36]=[N:35][C:34]([CH3:33])=[CH:42][CH:41]=2)=[O:39])[CH:7]=[CH:6][C:5]=1[C:8]1[C:9]([CH2:21][O:22][C:23]([C:25]2[S:26][C:27]([CH3:30])=[CH:28][CH:29]=2)=[O:24])=[C:10]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH3:18])([CH3:19])[CH:12]=[C:11]2[CH3:20]
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참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 1378606-Methylnicotinic acidHCID 250156246-(4-Hydroxy-2-methoxyphenyl)-5-(5-methylthiophen-2-ylcarbonyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline

생성물 1

HCID 248913366-[2-Methoxy-4-(6-methylpyridin-3-ylcarbonyloxy)phenyl]-5-(5-methylthiophen-2-ylcarbonyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline
수율 57%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-(4-Hydroxy-2-methoxyphenyl)-5-(5-methylthiophen-2-ylcarbonyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 3-2, 32.5 mg, 0.0723 mmol) and 6-methylnicotinoic acid (15.7 mg, 0.114 mmol) were dissolved in N,N-dimethylformamide (1 mL), N,N-diisopropylethylamine (35 μL, 0.201 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate (38.3 mg, 0.101 mmol) were added thereto, and then the mixture was stirred at room temperature overnight. Ethyl acetate (20 mL) was added to the reaction mixture, and then the mixture was washed with water (20 mL) and saturated brine (20 mL) successively. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (21.5 mg) as a gray amorphous product. (Yield 57%)

후처리

  1. washthe mixture was washed with water (20 mL) and saturated brine (20 mL) successively
  2. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-080b0316cb004ba3b456b9ec270415e1
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08563551B2

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