Diisopropylethylamine → HCID 67958371, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine	HCID 2733845	—
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 67958758	HCID 67958758	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 67958371	HCID 67958371	161.1%

Reaction Conditions

Temperature	60 °C

Reaction Steps

In a 8 mL vial the 6-(4-methylchroman-5-yl)oxypyridin-3-amine (Intermediate 213, 22.9 mg, 0.089 mmol) was dissolved in N,N-Dimethylformamide (3 mL) to give a pale yellow solution. DIPEA (0.069 mL, 0.394 mmol), N-{[(1,1-dimethylethyl)oxy]carbonyl}-2-methylalanine (60.0 mg, 0.295 mmol) and HATU (112 mg, 0.295 mmol) were added. The reaction mixture was shaken at 60° C. for 1 hour. The reaction mixture was evaporated in vacuo and the residue was purified by flash chromatography on silica gel using a column SNAP 25 g and cyclohexane/ethyl acetate from 3:1 to 1:2 as eluents affording the title compound (63.3 mg) as a colorless oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09346790B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-0e1e300a03e14dcbb091e2ea005805e4
Source note	uspto-grants-2016_05