Water → 6-((3-((4'-(4-Hydroxybutyl)-[1,1'-biphenyl]-4-yl)carbamoyl)phenyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide

HRID 1944910노트

반응식

HRID 1944910 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=1)=[CH:17][C:16]([S:29]([C:32]1[CH:33]=[C:34]([CH:57]=[CH:58][CH:59]=1)[C:35]([NH:37][C:38]1[CH:43]=[CH:42][C:41]([C:44]3[CH:49]=[CH:48][C:47]([CH2:50][CH2:51][CH2:52][C:53](OC)=[O:54])=[CH:46][CH:45]=3)=[CH:40][CH:39]=1)=[O:36])(=[O:31])=[O:30])=[CH:15][C:14]=2[CH3:60])(=[O:9])[NH2:8].O.[OH-].[Na+]>C1COCC1.CCOC(C)=O.C(Cl)Cl.CO>[OH:54][CH2:53][CH2:52][CH2:51][CH2:50][C:47]1[CH:48]=[CH:49][C:44]([C:41]2[CH:42]=[CH:43][C:38]([NH:37][C:35]([C:34]3[CH:33]=[C:32]([S:29]([C:16]4[CH:17]=[C:18]5[C:13](=[C:14]([CH3:60])[CH:15]=4)[N:12]=[CH:11][C:10]([C:7]([NH2:8])=[O:9])=[C:19]5[NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=4)(=[O:30])=[O:31])[CH:59]=[CH:58][CH:57]=3)=[O:36])=[CH:39][CH:40]=2)=[CH:45][CH:46]=1

참가 물질

8

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66988342Methyl 4-(4'-(3-((3-carbamoyl-4-((3-methoxyphenyl)amino)-8-methylquinolin-6-yl)sulfonyl)benzamido)-[1,1'-biphenyl]-4-yl)butanoate

생성물 1

HCID 669883466-((3-((4'-(4-Hydroxybutyl)-[1,1'-biphenyl]-4-yl)carbamoyl)phenyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide수율 43.1%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 21226129Dichloromethane methanol용매

실험 절차

Solid LiAlH4 (29 mg, 0.713 mmol) was added to a stirring solution of Intermediate 86 (265 mg, 0.357 mmol) in THF (5 mL) at 0° C. After stirring for an hour H2O (0.029 mL), 15% (w/v) NaOH (0.029 mL), and H2O (0.087 mL) were added in order then stirred for additional 1 h. The resulting suspension was diluted with EtOAc (10 mL) and the organic layer was washed with H2O (15 mL), brine (15 mL), dried over Na2SO4, and concentrated to give crude alcohol (224 mg) as yellow solid. Chromatography (9:1, CH2Cl2/MeOH) afforded the title compound (110 mg, 43%) as yellow solid. ES/MS calcd. for C41H39N4O6S+ 715.3. Found m/z=715.4 (M+H)+.

후처리

  1. additionwere added in order
  2. washthe organic layer was washed with H2O (15 mL), brine (15 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give crude alcohol (224 mg) as yellow solid

출처 및 근거

ORD 기록
ord-24b1e6fe44cd4a12ac05372068e6daef
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394829B2

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