Diisopropylethylamine → HCID 178488088, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-	HCID 83692	—
Reactant	4-Methoxybenzene-1,2-diamine dihydrochloride	HCID 3085161	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 178488088	HCID 178488088	79.2%

Reaction Steps

To a mixture of N-(tert-butoxycarbonyl)-N-methylglycine (1.00 g), 4-methoxybenzene-1,2-diamine dihydrochloride (1.16 g) and DMF (25 mL) were added HATU (2.41 g) and DIPEA (4.5 mL), followed by stirring at room temperature overnight. The reaction mixture was diluted with EtOAc, and washed with water and brine in this order. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. To the residue was added acetic acid (20 mL), followed by heating and stirring at 80° C. for 3 hours, and then concentrating under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: Hex/EtOAc=80/20-20/80) to obtain tert-butyl [(5-methoxy-1H-benzimidazol-2-yl)methyl]methylcarbamate (1.22 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08937087B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-c623af38d9474133bcbf89c1819ad1a7
Source note	uspto-grants-2015_01