2-Fluoroethyl bromide → benzyl(3R,4S)-3-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}-4-(2-fluoroethoxy)pyrrolidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	2-Fluoroethyl bromide	HCID 12982	—
Reactant	5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amine	HCID 10217073	—
Reactant	benzyl (3R,4S)-3-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}-4-hydroxypyrrolidine-1-carboxylate	HCID 58583248	—
Product	benzyl(3R,4S)-3-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}-4-(2-fluoroethoxy)pyrrolidine-1-carboxylate	HCID 58583297	—

Reaction Steps

Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amine but benzyl (3R,4S)-3-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}-4-hydroxypyrrolidine-1-carboxylate and 1-bromo-2-fluoro ethane, and making non-critical variations provided the title compound as a oil: 1H NMR (DMSO-d6) δ) 1.07, 1.14, 2.36, 2.65, 3.60, 3.72, 3.79, 3.82, 4.27, 4.42, 4254, 4.62, 5.09, 5.95, 6.98, 7.11, 7.25, 7.38; IR (diffuse reflectance) 2350 (w), 2337 (w), 2058 (w), 1952 (w), 1940 (w), 1710 (s), 1569, 1552, 1483 (s), 1459, 1419 (s), 1397, 1353, 1287, 1228, cm−1 HRMS (FAB) calcd for C29H34ClFN4O4+H 557.2330, found 557.2338.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06992087B2
Source dataset	uspto-grants-2006_01
ORD ID	ord-7ba82ccf7d534f3eb4d3e5204699d6c8
Source note	uspto-grants-2006_01