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

HRID 1944910Notes

Reaction equation

HRID 1944910 reaction equation
[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

Participants

8

Reactant 4

HCID 962Water2×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

Product 1

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

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-24b1e6fe44cd4a12ac05372068e6daef
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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