Cyclohexanemethylamine → 4-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carboxylic acid

https://huagongshe.com/reaction/1922190

Participants

Role	Name	HCID	Charge
Reactant	Cyclohexanemethylamine	HCID 76688	—
Reactant	N-methyl-4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)picolinamide	HCID 57725414	—
Reactant	4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide	HCID 57725559	—
Product	4-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carboxylic acid	HCID 57725514	—

Reaction Steps

In Scheme 5, 4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide is aminated with cyclohexylmethanamine. The resulting 4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide is then hydrolyzed to form 4-[2-(cyclohexylmethyl-amino)-benzooxazol-6-yloxy]-pyridine-2-carboxylic acid. 4-[2-(Cyclohexylmethyl-amino)-benzooxazol-6-yloxy]-pyridine-2-carboxylic acid then reacts with benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate, tert-butyl carbazate, and triethyl amine to form 4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carbohydrazide. 4-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carbohydrazide then reacts with trimethyl orthoformate to form a compound of the embodiments.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08173689B2
Source dataset	uspto-grants-2012_05
ORD ID	ord-5027318c6e8a48aba64e524fd2c64e5d
Source note	uspto-grants-2012_05