Water → 9-tert-butyl-2-bromo-3-methoxy-13-(2-thienyl)-5,6,9,10,11,12-hexahydro-8H-azepino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8-one

https://huagongshe.com/reaction/1971649

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Ammonium Hydroxide	HCID 14923	—
Reactant	Sodium Acetate	HCID 517045	—
Reactant	7-Bromo-2-(2-(tert-butyl(5-(thiophen-2-yl)pent-4-ynyl)amino)-2-oxoacetyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid	HCID 58124948	—
Solvent	Acetic Anhydride	HCID 7918	—
Product	9-tert-butyl-2-bromo-3-methoxy-13-(2-thienyl)-5,6,9,10,11,12-hexahydro-8H-azepino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8-one	HCID 58124852	85.3%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A solution of 2.9 g of 3c in 30 ml of acetic anhydride and 3 g of sodium acetate was heated with stirring at 100° C. for ½ hr. The mixture was cooled to RT. Then, 100 ml of water was added and stirring was prolonged for 1 hr. The reaction mixture was neutralized by dropwise addition of cold conc. aq. NH4OH solution, the product was extracted with ethyl acetate and the organic layer was washed, dried and concentrated. The residue was treated with diisopropyl ether, to provide 2.2 g of 3d as white crystalline material; Mp 232-233° C.; MS-ESI: [M+1] 499.15 and 501.19. Rf (heptane/ethyl acetate 1/1) 0.50

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08431564B2
Source dataset	uspto-grants-2013_04
ORD ID	ord-3cc0f1cee6b7424cb14903caf48e3fbc
Source note	uspto-grants-2013_04