Diisopropylethylamine → (+)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-methyl-isonicotinamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	2-methylpyridine-4-carboxylic Acid Hydrochloride	HCID 2762824	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	(+)-7-[1,4)Dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine	HCID 22507697	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(+)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-methyl-isonicotinamide	HCID 11292077	66%

Reaction Steps

To a stirred solution of 85 mg (0.49 mmol) 2-methyl-isonicotinic acid hydrochloride in 10 ml THF were added 214 mg (0.56 mmol) HATU and 0.16 ml (0.94 mmol) N-ethyldiisopropylamine and stirring continued at room temperature for 1 h. 100 mg (0.38 mmol) (±)-7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine was then added and stirring continued at room temperature for 24 h. The reaction mixture was then poured into saturated aqueous sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Trituration in ether afforded 95 mg (66%) (±)-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-2-methyl-isonicotinamide as a white solid. ES-MS m/e (%): 386 (M+H+, 100).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06872833B2
Source dataset	uspto-grants-2005_03
ORD ID	ord-3d09a5acb9124f5fb3e7a82b7d1007ac
Source note	uspto-grants-2005_03