Diisopropylethylamine → N-(5-Chloro-3-fluoropyridin-2-yl)-2-((2-chloro-6-fluorophenyl)amino)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	(1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate	HCID 75951468	—
Reactant	HCID 178422815	HCID 178422815	—
Reactant	HCID 178507977	HCID 178507977	—
Catalyst	Iron	HCID 23925	—
Solvent	Acetic Acid	HCID 176	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-(5-Chloro-3-fluoropyridin-2-yl)-2-((2-chloro-6-fluorophenyl)amino)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxamide	HCID 178422805	13.4%

Reaction Steps

The title compound was prepared by following the procedure described for Example-121 using 2-[(2-chloro-6-fluorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-15, 0.200 g, 0.266 mmol), COMU (0.569 g, 0.663 mmol), DIPEA (0.732 g, 5.66 mmol), 2-amino-5-chloro-3-fluoropyridine 1-oxide (Intermediate-43, 0.095 g, 0.584 mmol), DMF (3.0 mL), iron powder (0.200 g, 3.57 mmol) and acetic acid (10.0 mL) to afford 0.018 g of the desired product. 1HNMR (DMSO-d6): δ 1.54 (s, 6H), 3.10 (s, 2H), 7.30 (m, 3H), 7.40 (m, 1H), 8.17 (d, J=9.3 Hz, 1H), 8.36 (s, 1H), 9.85 (s, 1H), 11.00 (2H); MS [M]+: 504.04.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08519149B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-927cd3680ec64977a84235e828feba3c
Source note	uspto-grants-2013_08