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Hydrochloric Acid → HCID 59321574, 화합물

HRID 2423525
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HRID 2423525 반응식
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[C:29]([CH3:34])[C:28]([C:35]([O:37]CC)=[O:36])=[CH:27]4)=[CH:20][CH:19]=2)=[C:14]([CH:40]([CH3:42])[CH3:41])[O:13][N:12]=1.Cl.O>O1CCCC1.CO>[Cl:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[C:5]=1[C:11]1[C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[C:29]([CH3:34])[C:28]([C:35]([OH:37])=[O:36])=[CH:27]4)=[CH:20][CH:19]=2)=[C:14]([CH:40]([CH3:42])[CH3:41])[O:13][N:12]=1
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 59321567HCID 59321567, 화합물

생성물 1

HCID 59321574HCID 59321574, 화합물수율 99%

시약·촉매·용매 2

HCID 887Methanol용매
HCID 8028
Tetrahydrofuran
용매

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온도
90 °C

실험 절차

A 1 N solution of sodium hydroxide (92.8 μL, 92.8 μmol) was added to ethyl 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-methyl-3-quinolinecarboxylate (26.7 mg, 46.4 μmol) in tetrahydrofuran and methanol (1:1, 927.9 μL) and the mixture was heated in the microwave at 90° C. for 10 minutes. After cooling, the mixture was neutralized with 1 N hydrochloric acid (92.8 μL), water was added, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, then dried over anhydrous magnesium sulfate, filtered and concentrated to give 25.1 mg (99%) of 6-[4-({[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-methyl-3-quinolinecarboxylic acid as a solid. 1H NMR (400 MHz, d6-DMSO): δ 13.31 (br s, 1H), 8.86 (s, 1H), 8.29 (d, J=2 Hz, 1H), 8.09 (dd, J=9, 2 Hz, 1H), 7.98 (d, J=9 Hz, 1H), 7.69 (d, J=9 Hz, 2H), 7.66-7.60 (m, 2H), 7.55 (dd, J=9, 7 Hz, 1H), 6.93 (d, J=9 Hz, 2H), 4.88 (s, 2H), 3.47 (septet, J=7 Hz, 1H), 2.86 (s, 3H), 1.34 (d, J=7 Hz, 6H). HRMS C30H24Cl2N2O4 m/z 547.1191 (M+H)+Cal; 547.1191 (M+H)+Obs.

후처리

  1. temperatureAfter cooling
  2. additionwas added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b64c013f8b69405cb6d5405da59b20c4
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960552B2

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