2-Amino-4-methylthiazole → 6-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}-N-(4-methyl-1,3-thiazol-2-yl)imidazo[2,1-b][1,3]thiazole-5-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	2-Amino-4-methylthiazole	HCID 74143	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	6-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid	HCID 67549485	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	6-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}-N-(4-methyl-1,3-thiazol-2-yl)imidazo[2,1-b][1,3]thiazole-5-carboxamide	HCID 46832952	—

Reaction Steps

The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 3 (250 mg, 0.646 mmol) with 4-methyl-1,3-thiazol-2-amine (82 mg, 0.711 mmol) in the presence of EDCI hydrochloride (247 mg, 1.292 mmol) and DMAP (36.33 mg, 0.323 mmol) in a mixture of DCM and DMF (4:1, 10 mL) to give 110 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.06 (s, 9H), 2.28 (s, 3H), 3.57 (s, 2H), 3.80 (s, 3H), 6.62 (s, 1H), 6.98 (d, J=7.8 Hz, 1H), 7.11 (t, J=7.8 Hz, 1H), 7.36-7.40 (m, 2H), 7.88 (d, J=16.2 Hz, 1H), 7.98-8.20 (br m, 1H), 8.55 (br m, 1H), 12.89 (br s, 1H); ESI-MS (m/z) 483.33 (MH)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08318928B2
Source dataset	uspto-grants-2012_11
ORD ID	ord-70d14f66de954e7fa8bc251cdea06391
Source note	uspto-grants-2012_11