Diisopropylethylamine → tert-butyl 2-(N-(4-(2-(4-bromophenyl)oxazol-4-yl)benzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetate

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Sodium Bicarbonate	HCID 516892	—
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	Tert-butyl 2-((4-(2-(4-bromophenyl)oxazol-4-yl)benzyl)amino)acetate	HCID 71076724	—
Reactant	4-(2-(4-Methoxy-2-(trifluoromethyl)phenyl)acetamido)benzoic acid	HCID 71076743	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Product	tert-butyl 2-(N-(4-(2-(4-bromophenyl)oxazol-4-yl)benzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetate	HCID 71076598	68%

Reaction Steps

To a stirring solution of tert-butyl 2-((4-(2-(4-bromophenyl)oxazol-4-yl)benzyl)amino)acetate INT-44 (220 mg, 0.496 mmol), 4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzoic acid (175 mg, 0.496 mmol) and DIEA (137 μl, 0.744 mmol) in DMF (4 mL) was added HATU (198 mg, 0.521 mmol). The reaction mixture was stirred at room temperature for 16 h then diluted with DCM (4 mL), stirred with NaHCO3 (15 mL) for 15 min, split through a hydrophobic frit and evaporated. The crude product was purified by column chromatography (acetonitrile/DCM) to gave 262 mg (68%) of tert-butyl 2-(N-(4-(2-(4-bromophenyl)oxazol-4-yl)benzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetate INT-45 as an off-white solid. LCMS-ESI (m/z) calculated for C39H35BrF3N3O6: 777; found 778 [M+H]+, tR=3.20 min (Method 5).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09278910B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-32c8e73ddc104d4689d93664c02ae8f5
Source note	uspto-grants-2016_03