Sodium Bicarbonate → Trifluoroacetic acid

Participants

Role	Name	HCID	Charge
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	tert-butyl methyl(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)carbamate	HCID 90412594	—
Product	Trifluoroacetic acid	HCID 6422	111%
Product	N-methyl-2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)ethanamine	HCID 90411907	—

Reaction Steps

The title compound was prepared from tert-butyl methyl(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenethyl)carbamate (CB63), neutralized with aqueous sodium bicarbonate, and isolated as a yellow waxy solid with excess trifluoroacetic acid (5.73 g, 111%): 1H NMR (400 MHz, CDCl3) δ 8.53 (s, 1H), 8.12 (d, J=8.2 Hz, 2H), 7.77 (d, J=9.0 Hz, 2H), 7.37 (dd, J=9.0, 1.0 Hz, 2H), 7.31 (d, J=8.2 Hz, 2H), 3.23-3.12 (m, 2H), 3.05 (dd, J=9.4, 6.3 Hz, 2H), 2.67 (s, 3H), 1.29-1.22 (m, 1H); 19F NMR (376 MHz, CDCl3) δ −58.04, −75.71; ESIMS m/z 363 ([M+H]+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09278964B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-10d632b3f4d24e3bbfdd38467c904930
Source note	uspto-grants-2016_03