Potassium Carbonate → Ethyl 4-{[4-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridin-2-yl)-3,4-dihydro-2h-1,4-benzoxazin-6-yl]amino}-1-methyl-1h-imidazole-2-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	L-Proline	HCID 145742	—
Reactant	ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate hydrochloride	HCID 22349687	—
Reactant	2-(6-Bromo-2,3-dihydrobenzo[1,4]oxazin-4-yl)-6,6-dimethyl-6,7-dihydro-[1,3]thiazolo[5,4-d]pyridin-4(5h)-one	HCID 68597236	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	Ethyl 4-{[4-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridin-2-yl)-3,4-dihydro-2h-1,4-benzoxazin-6-yl]amino}-1-methyl-1h-imidazole-2-carboxylate	HCID 67186781	3.6%

Reaction Steps

A mixture of Example 39 (0.4 g, 1.015 mmol), copper(I) iodide (0.038 g, 0.203 mmol), potassium carbonate (0.420 g, 3.04 mmol), proline (0.045 g, 0.406 mmol) and 4-amino-1-methylimidazole-2-carboxylic acid ethyl ester hydrochloride (0.417 g, 2.03 mmol) in DMSO (3 mL) was heated to 120° C. for 16 h in a sealed tube. It was concentrated in vacuo and purified by preparative HPLC (Method 6) to give the title compound (0.007 g, 1.6%) as a yellow solid. δH (DMSO-d6) 8.39 (1H, s), 7.99 (1H, d, J 2.1 Hz), 7.52 (1H, s), 7.06 (1H, s), 6.83-6.76 (2H, m), 4.32-4.18 (4H, m), 4.10-4.01 (2H, m), 3.92 (3H, s), 2.83 (2H, s), 1.32-1.22 (9H, m). LCMS (ES+) 483/484 (M+H)+, RT 2.94 minutes (Method 1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08242116B2
Source dataset	uspto-grants-2012_08
ORD ID	ord-ba9a5e751c5e4cb3b019b5cb2884df22
Source note	uspto-grants-2012_08