Diisopropylethylamine → HCID 123384314, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	(1S,4R)-4-[3-((S)-2-Methyl-piperidin-1-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-ylamine	HCID 86687106	—
Reactant	HCID 123151394	HCID 123151394	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 123384314	HCID 123384314	60.4%

Reaction Conditions

Temperature	70 °C

Reaction Steps

Intermediate B (0.23 g, 0.61 mmol) was treated with a solution of Intermediate 74g (0.47 g, 0.68 mmol) in 1,4-dioxane (3.4 mL) then DIPEA (0.13 mL, 0.74 mmol) was added. The mixture was stirred at 70° C. overnight. The mixture was evaporated in vacuo and the residue was partitioned between DCM and water. The aqueous layer was then extracted with DCM (2×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-7% MeOH in DCM, to give the title compound (0.34 g, 60%). LCMS (Method 3): Rt 5.48 min, m/z 923.7 [MH+].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181242B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-f5e8a0651f9f4c69ae093fd2e397ee95
Source note	uspto-grants-2015_11