Sodium Hydroxide → HCID 57503214, compound

HRID 504696Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH:9]1[S:13][C:12]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[N:23]([CH3:32])[S:24]([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)(=[O:26])=[O:25])=[N:11][CH2:10]1)#[N:8].[OH-].[Na+]>O1CCCC1>[NH2:8][CH2:7][CH:9]1[S:13][C:12]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[N:23]([CH3:32])[S:24]([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)(=[O:26])=[O:25])=[N:11][CH2:10]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of lithium aluminum hydride (0.015 g) in tetrahydrofuran (2 ml) was added dropwise a solution of N-[2-(5-cyano-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide (0.080 g) in tetrahydrofuran (3 ml) under ice-cooling, and the reaction mixture was stirred at 0° C. for 2 hr. 1N Aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=80:20-100:0), and recrystallized from hexane-ethyl acetate to give the title compound (0.029 g, yield 36%) as colorless crystals.

Workup

temperaturecooling
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=80:20-100:0)
customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record: ord-d6026196c56648cd82644811d5eeb650
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07777047B2

Reaction notes

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