Ethyl Acetate → HCID 59425155, compound

HRID 506058Notes

Reaction equation

C([O:4][CH2:5][CH2:6][N:7]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:19]([CH2:31][CH3:32])[C:20]3[C:25]([C:26]=2[C:27]#[N:28])=[CH:24][CH:23]=[C:22]([O:29][CH3:30])[CH:21]=3)=[CH:14][CH:13]=1)[S:8]([CH3:11])(=[O:10])=[O:9])(=O)C.O.[OH-].[Li+].C(OCC)(=O)C>C1COCC1>[C:27]([C:26]1[C:25]2[C:20](=[CH:21][C:22]([O:29][CH3:30])=[CH:23][CH:24]=2)[N:19]([CH2:31][CH3:32])[C:18]=1[C:15]1[CH:14]=[CH:13][C:12]([N:7]([CH2:6][CH2:5][OH:4])[S:8]([CH3:11])(=[O:10])=[O:9])=[CH:17][CH:16]=1)#[N:28]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N-(2-acetoxyethyl)-N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]methanesulfonamide (compound 815, 164 mg, 0.360 mmol) and lithium hydroxide hydrate (45 mg, 1.07 mmol) in 5 mL THF/1 mL water is warmed to 60° C. overnight. The mixture is cooled and poured into ethyl acetate (50 mL). This is washed with water (50 mL) and brine (20 mL), dried over anhydrous magnesium sulfate, filtered and evaporated to afford a solid. The solid is triturated with ether, collected by filtration and dried under high vacuum to afford N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-N-(2-hydroxyethyl)methanesulfonamide, compound 828 (137 mg, 0.331 mmol, 92%).

Workup

temperatureThe mixture is cooled
washThis is washed with water (50 mL) and brine (20 mL)
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customevaporated
customto afford a solid
customThe solid is triturated with ether
filtrationcollected by filtration
customdried under high vacuum

Sources & evidence

ORD record: ord-92006f397fb6449fa7e523546e67eaaf
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781478B2

Reaction notes

Loading…