Diisopropylethylamine → HCID 67332211, compound

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-(4-methylphenyl)-1,3-benzoxazol-5-amine	HCID 721879	—
Reactant	4,4,4-Trifluorobutanoic acid	HCID 2777085	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 67332211	HCID 67332211	8.5%

Reaction Steps

To 4,4,4-trifluorobutanoic acid (128 mg, 0.90 mmol) in dry dimethylformamide (5 mL) was added HATU (397 mg, 1.05 mmol) and diisopropylethylamine (496 μL, 2.85 mmol). The mixture was then stirred at room temperature for 10 min. 2-p-Tolylbenzo[d]oxazol-5-amine (200 mg, 0.95 mmol) was then added and the resulting mixture was stirred at room temperature for 16 h. Ethyl acetate was added and the organic layer was washed once with saturated aqueous Na2CO3, followed by another wash with brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 40:60 v/v to afford 26.7 mg (8%) of the title compound (LCMS RT=6.77 min, MH+ 348.9)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08518980B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-61048e0d7e484af19e14a0cb837352fc
Source note	uspto-grants-2013_08