4-((2S)-3-Amino-2-hydroxy-propoxy)-phenol → 5-(4-{4-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-piperidin-1-yl}-benzylidene)-2-piperidin-1-yl-thiazol-4-one

Participants

Role	Name	HCID	Charge
Reactant	4-((2S)-3-Amino-2-hydroxy-propoxy)-phenol	HCID 9877547	—
Reactant	1-[4-(4-oxo-2-piperidin-1-yl-4H-thiazol-5-ylidenemethyl)-phenyl]-piperidin-4-one	HCID 69922636	—
Product	5-(4-{4-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-piperidin-1-yl}-benzylidene)-2-piperidin-1-yl-thiazol-4-one	HCID 69921091	—

Reaction Steps

The title compound was prepared from 1-[4-(4-oxo-2-piperidin-1-yl-4H-thiazol-5-ylidenemethyl)-phenyl]-piperidin-4-one (which was obtained in Intermediate 25) and 4-((2S)-3-amino-2-hydroxy-propoxy)-phenol (which was obtained in Intermediate 5) according to the procedure of Example 1 as a yellowish solid; mp>85° C. (dec.); 1 H NMR (300 MHz, DMSO-d6) δ1.20-1.40 (m, 2 H), 1.55-1.70 (m, 6 H), 1.85-2.00 (m, 2 H), 2.55-2.95 (m, 6 H), 3.60 (br s, 2 H), 3.70-3.95 (m, 6 H), 6.66 (d, J=9.0 Hz, 2 H), 6.75 (d, J=9.0 Hz, 2 H), 7.02 (d, J=9.0 Hz, 1 H), 7.48 (d, J=9.0 Hz, 1 H), 7.50 (s, 1 H), 8.90 (brs, 1 H); MS (ES) m/z: 269.0 ((M+2H)2+, 100%); 537.6 (MH+, 10%); HRMS Calcd. for C29H37N4O4S (MH+): 537.2536. Found: 537.2500.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06410734B1
Source dataset	uspto-grants-2002_06
ORD ID	ord-1a726ecf47364c7cb553e30c0fb612d4
Source note	uspto-grants-2002_06