5-(1,1-Difluoroethyl)pyrazine-2-carboxylic acid → N-(3-((4aS,5S,7aS)-2-amino-5-(trifluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-(1,1-difluoroethyl)pyrazine-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	5-(1,1-Difluoroethyl)pyrazine-2-carboxylic acid	HCID 66869549	—
Reactant	tert-butyl[(4aS,5S,7aS)-7a-(5-amino-2-fluorophenyl)-5-trifluoromethyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl]carbamate	HCID 68171522	—
Product	N-(3-((4aS,5S,7aS)-2-amino-5-(trifluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-7a-yl)-4-fluorophenyl)-5-(1,1-difluoroethyl)pyrazine-2-carboxamide	HCID 57523783	—

Reaction Steps

Synthesized from tert-butyl[(4aS,5S,7aS)-7a-(5-amino-2-fluorophenyl)-5-trifluoromethyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl]carbamate and 5-(1,1-difluoroethyl)pyrazine-2-carboxylic acid according to the general procedure. 1H NMR (600 MHz, CDCl3) δ ppm 2.03 (t, J=18.8 Hz, 3 H), 2.82 (d, J=12.0 Hz, 1 H), 3.14 (d, J=12.4 Hz, 1 H), 3.35-3.46 (m, 1 H), 3.77-4.07 (m, 1 H), 4.20-4.93 (m, 4 H), 7.08 (dd, J=11.7, 9.0 Hz, 1 H), 7.56 (d, J=4.5 Hz, 1 H), 7.80-7.93 (m, 1 H), 8.87 (s, 1 H), 9.43 (s, 1 H), 9.59 (br. s., 1 H)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08940734B2
Source dataset	uspto-grants-2015_01
ORD ID	ord-99baeb59c8b7494081c05ca080dfa7be
Source note	uspto-grants-2015_01