Ethyl Acetate → HCID 59425155, compound

HRID 252550Notes

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-4febe839ce54434c9d4a96f6cf4d7316
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868037B2

Reaction notes

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