(4-Methoxy-2-methylphenyl)boronic acid → trans-(+/-)-4-{[3,6-Diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}tetrahydrofuran-3-ol

Participants

Role	Name	HCID	Charge
Reactant	(4-Methoxy-2-methylphenyl)boronic acid	HCID 2773486	—
Reactant	(1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol	HCID 58583246	—
Reactant	trans-(+/-)-4-[(5-Bromo-3,6-diethylpyrazin-2-yl)amino]tetrahydrofuran-3-ol	HCID 86588872	—
Product	trans-(+/-)-4-{[3,6-Diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}tetrahydrofuran-3-ol	HCID 86588873	—

Reaction Steps

Following the procedure for the preparation of (1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol but substituting trans-(+/−)-4-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]tetrahydrofuran-3-ol and 2-methyl-4-methoxyphenylboronic acid and making non-critical variations provided the title compound as a light yellow solid. IR (diffuse reflectance) 3363, 1603, 1571, 1490, 1447, 1393, 1303, 1233, 1208, 1177, 1170, 1103, 1059, 887, 849 cm−1; OAMS supporting ions at: ESI+ 358.1; MS (EI) m/z 357 (M+); HRMS (FAB) calcd for C20H27N3O3+H1 358.2130, found 358.2142.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06992087B2
Source dataset	uspto-grants-2006_01
ORD ID	ord-decd676da8b64ea5bd7bd980dbd44512
Source note	uspto-grants-2006_01