Water → HCID 66988709, compound

HRID 1944946Notes

Reaction equation

HRID 1944946 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:39]=[CH:40][CH:41]=1)[C:35](OC)=[O:36])(=[O:31])=[O:30])=[CH:15][C:14]=2[CH3:42])(=[O:9])[NH2:8].O.[OH-].[Na+]>C1COCC1>[OH:36][CH2:35][C:34]1[CH:33]=[C:32]([S:29]([C:16]2[CH:17]=[C:18]3[C:13](=[C:14]([CH3:42])[CH:15]=2)[N:12]=[CH:11][C:10]([C:7]([NH2:8])=[O:9])=[C:19]3[NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)(=[O:31])=[O:30])[CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 11489006HCID 11489006, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 66988709HCID 66988709, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LAH (158 mg, 3.96 mmol) was added to a stirring solution of methyl 3-[[3-carbamoyl-4-[(3-methoxyphenyl)amino]-8-methylquinolin-6-yl]sulfonyl]benzoate (500 mg, 0.99 mmol) in THF (10 mL) at 0° C. After stirring for 20 min, H2O (0.158 mL), 15% (w/v) NaOH (0.158 mL), and H2O (0.474 mL) were added sequentially. The resulting suspension was stirred for 1 h then the precipitate was filtered, washed with water (20 mL), and dried to give the title compound (330 mg) as a yellow solid. The compound was used with no further purification. ES/MS calcd. for C25H24N3O5S+ 478.1. Found m/z=478.1 (M+H)+.

Workup

  1. stirringThe resulting suspension was stirred for 1 h
  2. filtrationthe precipitate was filtered
  3. washwashed with water (20 mL)
  4. customdried

Sources & evidence

ORD record
ord-b7b41e970e494b6488c8f44bf3f5d1af
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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