2-Aminothiazole → 2-(1,3-dioxoisoindolin-2-yl)-4-methyl-N-(thiazol-2-yl)pentanamide

Participants

Role	Name	HCID	Charge
Reactant	2-Aminothiazole	HCID 2155	—
Reactant	Triethylamine	HCID 8471	—
Reactant	2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-methylpentanoic acid	HCID 102808	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(1,3-dioxoisoindolin-2-yl)-4-methyl-N-(thiazol-2-yl)pentanamide	HCID 2831706	—

Reaction Steps

Referring to Scheme 3, a mixture of 2-(1,3-dioxoisoindolin-2-yl)-4-methylpentanoic acid (78 mg, 0.3 mmol), 2-aminothiazole (30 mg, 0.3 mmol), HBTU (114 mg, 0.3 mmol) and 0.1 mL of Et3N in DMF (2 mL) was stirred at room temperature for 2 hours to provide the title compound, which was then purified by HPLC. 1H NMR (400 MHz, MeOH-d4) δ: 7.83-7.86 (m, 2H), 7.89-7.92 (m, 2H), 7.41 (d, J=3.2 Hz, 1H), 7.12 (d, J=3.2 Hz, 1H), 5.15 (dd, J=4.8, 11.6 Hz, 2H), 2.35-2.45 (m, 1H), 1.96-2.05 (m, 1H), 1.51 (m, 1H), 0.99 (d, J=6.4 Hz, 3H), 0.95 (d, J=6.4 Hz, 3H). [M+H] calc'd for C17H17N3O3S, 344. found, 344.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08008332B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-10f4c01c459d409181a6b5bb2bc5d515
Source note	uspto-grants-2011_08