Tetrahydrofuran → N-{2-[5-(aminomethyl)-5-methyl-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide

HRID 1994896Notes

Reaction equation

HRID 1994896 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[C:12]([C:14]1([CH3:38])[S:18][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][C:22]=3[N:28]([CH3:37])[S:29]([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)(=[O:31])=[O:30])=[N:16][CH2:15]1)#[N:13].[OH-].[Na+]>C(O)C>[NH2:13][CH2:12][C:14]1([CH3:38])[S:18][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][C:22]=3[N:28]([CH3:37])[S:29]([C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)(=[O:31])=[O:30])=[N:16][CH2:15]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59135902N-[2-(5-cyano-5-methyl-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide

Product 1

HCID 59135762N-{2-[5-(aminomethyl)-5-methyl-4,5-dihydro-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamideYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of lithium aluminum hydride (0.05 g) and tetrahydrofuran (6 mL) was added N-[2-(5-cyano-5-methyl-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide (0.40 g) at 0° C., and the mixture was stirred for 15 min. Ethanol (2 mL) and 1N aqueous sodium hydroxide solution (0.2 mL) were successively added, and the resulting inorganic salt was removed by filtration. The filtrate was concentrated, and the residue was subjected to basic silica gel column chromatography to give the title compound (0.23 g, yield 57%) as colorless crystals from a fraction eluted with ethyl acetate. melting point 164-165° C.

Workup

  1. customthe resulting inorganic salt was removed by filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-740c6eebb8b440a6a8cbf28ad7db5802
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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