Triethylamine → HCID 66892955, compound

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	4-Nitrobenzoyl chloride	HCID 8502	—
Reactant	Tert-butyl 3-hydroxyazetidine-1-carboxylate	HCID 2756801	—
Reactant	5-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indoline	HCID 66709668	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 66892955	HCID 66892955	—

Reaction Steps

3-Hydroxy-azetidine-1-carboxylic acid tert-butyl ester (0.17 g, 1 mmol) was dissolved in 3 mL of DCM with triethylamine (0.28 mL, 2 mmol). 4-Nitro-benzoyl chloride (0.2 g, 1 mmol) was added and the mixture was stirred at room temperature for 12 h. A fifth of the solution was reacted with 4b (75 mg, 0.2 mmol). The mixture was stirred at room temperature for 8 h, diluted with DCM and washed with saturated NaHCO3. The organic layer was evaporated to afford crude 22a, LCMS 574.2 (MH+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08481731B2
Source dataset	uspto-grants-2013_07
ORD ID	ord-1c74066d8f7740f69c5c780c4855940b
Source note	uspto-grants-2013_07