5-Difluoromethympyrazine-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-(difluoromethyl)pyrazine-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	5-Difluoromethympyrazine-2-carboxylic acid	HCID 57468575	—
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-(difluoromethyl)pyrazine-2-carboxamide	HCID 57524928	—

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-difluoromethyl-pyrazine-2-carboxylic acid according to the general procedure. 1 H NMR (400 MHz, CDCl3) δ ppm 2.80 (dd, J=13.8, 3.7 Hz, 1 H), 3.11 (dd, J=13.6, 2.8 Hz, 1 H), 3.31-3.41 (m, 1 H), 3.86 (d, J=8.3 Hz, 1 H), 4.57 (d, J=8.3 Hz, 1 H), 4.64 (dt, J=14.7, 7.1 Hz, 1 H), 4.75 (br s, 2 H), 6.69 (t, J=56.3 Hz, 1 H), 7.07 (dd, J=11.6, 8.8 Hz, 1 H), 7.57 (dd, J=7.1, 2.8 Hz, 1 H), 7.87 (dt, J=8.5, 3.6 Hz, 1 H), 8.85 (s, 1 H), 9.45 (s, 1 H), 9.58 (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-9137c61f86034c26bcc836452bd5659d
Source note	uspto-grants-2015_01