Dimethylformamide → 2-Bromo-6-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6), 7-dien-10-yl}-4-fluoro-N-methylbenzamide

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Methylamine hydrochloride	HCID 6364545	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	2-Bromo-6-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-4-fluorobenzoic Acid	HCID 86683775	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Triethylamine	HCID 8471	—
Product	2-Bromo-6-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6), 7-dien-10-yl}-4-fluoro-N-methylbenzamide	HCID 86683776	70%

Reaction Conditions

Temperature	25 °C

Reaction Steps

A 25-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with DMF (8 mL), 129a (160 mg, 0.38 mmol), HATU (505 mg, 1.33 mmol), DMAP (46 mg, 0.38 mmol), and triethylamine (1.0 mL). The mixture was heated at 25° C. for 0.5 h. Then MeNH2.HCl (266 mg, 3.8 mmol) was added and resulting mixture was stirred at 25° C. for 2.5 h. After this time the reaction was cooled to room temperature. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by prep-TLC developing with 1:20 methanol/dichloromethane to afford 129b (116 mg, 70%) as a black solid. MS-ESI: [M+H]+ 434.0

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946213B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-6f6c72d99aca48459572565e86a77113
Source note	uspto-grants-2015_02