p-Toluenesulfonic acid monohydrate → 2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)-N-(3-nitro-4-(4-oxo cyclohexylamino)phenylsulfonyl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	p-Toluenesulfonic acid monohydrate	HCID 521998	—
Reactant	n-(4-(1,4-Dioxaspiro[4.5]decan-8-ylamino)-3-nitrophenylsulfonyl)-2-(1h-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)benzamide	HCID 56591433	—
Solvent	Acetone	HCID 180	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-(4-((2-(4-chlorophenyl)-4,4-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)-N-(3-nitro-4-(4-oxo cyclohexylamino)phenylsulfonyl)benzamide	HCID 67127111	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

To a solution of EXAMPLE 340B (386 mg) in acetone (10 mL) and water (5 mL) was added para-toluenesulfonic acid monohydrate (50 mg). The mixture was stirred at 120° C. in a Biotage Initiator microwave reactor for 30 minutes. The mixture was diluted with dichloromethane (300 mL) and washed with aqueous NaHCO3, water, brine and dried over Na2SO4. Filtration and evaporation of the solvent gave the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08546399B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-61362fcccc5543f4bdd992167b519f2e
Source note	uspto-grants-2013_10