Diisopropylethylamine → HCID 23146362, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Methyl-1,3-thiazole-4-carboxylic acid	HCID 284728	—
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	HCID 23146301	HCID 23146301	—
Reactant	HCID 23146330	HCID 23146330	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 23146362	HCID 23146362	—

Reaction Steps

The mixture of 2-piperidin-2-ylmethyl-5,6,7,8-tetrahydro-[1,2,4]-triazolo[1,5-a]pyridine and 2-piperidin-2-ylmethyl-[1,2,4]-triazolo[1,5-a]pyridine, D34 (0.220 g) was treated with HATU (0.380 g), N,N-diisopropylethylamine (1.0 ml) and 5-4-fluorophenyl)-2-methylthiazole-4-carboxylic acid (0.240 g) in dry DMF, according to the procedure described in Example 60. The crude product was chromatographed (silica gel, 4% methanol-diethyl ether) to afford 1-[5-(4-fluoro-phenyl)-2-methylthiazol-4-yl]-1-(2-[1,2,4]-triazolo[1,5-a]pyridin-2-ylmethylpiperidin-1-yl)-methanone as a colourless foam (0.070 g) (Mass spectrum (API30 ): found 436(MH+): C23H22FN5OS requires 435). Continued elution (10% methanol diethyl ether) afforded 1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-1-[2-(5,6,7,8-tetrahydro-[1,2,4]-triazolo[1,5-a]-pyridin-2-ylmethyl)piperidin-1-yl]-methanone as a colourless foam (0.230 g) (Mass spectrum (API+): found 440(MH+): C23H26FN5OS requires 439).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07470710B2
Source dataset	uspto-grants-2008_12
ORD ID	ord-e482890902b04a31896fed2e7dc790c5
Source note	uspto-grants-2008_12