Ethanolamine → 6-chloro-4'-{5-chloro-2-[1-(2-hydroxy-ethylcarbamoyl)-1-methyl-ethoxy]-phenyl}-2'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Participants

Role	Name	HCID	Charge
Reactant	Ethanolamine	HCID 700	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	6-chloro-4'-[5-chloro-2-(2-hydroxy-1,1-dimethyl-ethoxy)phenyl]-2'-[5-fluoro-2-methylphenyl]spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione	HCID 76567885	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	6-chloro-4'-{5-chloro-2-[1-(2-hydroxy-ethylcarbamoyl)-1-methyl-ethoxy]-phenyl}-2'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione	HCID 74928685	24.4%

Reaction Steps

To a mixture of racemic (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(2-hydroxy-1,1-dimethyl-ethoxy)phenyl]-2′-[5-fluoro-2-methylphenyl]spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (35 mg, 0.06 mmol), EDCl (18 mg, 0.094 mmol), HOBt (14 mg, 0.094 mmol) and DIPEA (23 mg, 0.2 mmol) in THF (1 mL) was added 2-amino-ethanol (11 mg, 0.18 mmol). The mixture was stirred at room temperature overnight, purified by prep-HPLC to give the title compound as a white solid (9 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07776875B2
Source dataset	uspto-grants-2010_08
ORD ID	ord-bfaff714be0c4334970afa2388b1762a
Source note	uspto-grants-2010_08