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

HRID 1944910ノート

反応式

HRID 1944910 の反応式
[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

参加物

8

反応物 4

HCID 962Water2 回HCID 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-24b1e6fe44cd4a12ac05372068e6daef
出典データセット
uspto-grants-2013_03
特許番号
US08394829B2

反応ノート

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