Water → HCID 57901824, compound

HRID 1851582Notes

Reaction equation

HRID 1851582 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:29]=1[NH:28][C:27]([C:30]1[S:31][CH:32]=[CH:33][N:34]=1)=[CH:26]2)[S:9]([C:12]1[CH:16]=[CH:15][S:14][C:13]=1[C:17](OC)=[O:18])(=[O:11])=[O:10].O.[OH-].[Na+]>O1CCCC1>[OH:18][CH2:17][C:13]1[S:14][CH:15]=[CH:16][C:12]=1[S:9]([N:8]([CH3:7])[C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:29]=1[NH:28][C:27]([C:30]1[S:31][CH:32]=[CH:33][N:34]=1)=[CH:26]2)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57901595HCID 57901595, compound

Product 1

HCID 57901824HCID 57901824, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (260 mg) in tetrahydrofuran (10 mL) was added dropwise a solution of methyl 3-({methyl[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]amino}sulfonyl)thiophene-2-carboxylate (1.4 g) in tetrahydrofuran (5 mL) under ice-cooling, and the mixture was stirred at room temperature for 4 hr. To the reaction mixture were added water (260 μL), 15% aqueous sodium hydroxide solution (260 μL) and water (780 μL) in this order and the mixture was stirred at room temperature for 2 hr. The insoluble material was filtered off, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound (701 mg, yield 54%) as pale-yellow crystals. melting point 192° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-baabe09d4a2749879d788c3e787f6755
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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