N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide → HCID 178525470, compound

Participants

Role	Name	HCID	Charge
Reactant	N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide	HCID 9837752	—
Reactant	4-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-one	HCID 10799105	—
Reactant	diethyl (2S)-2-[[5-[[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]methylidene]-4-oxo-1,3-thiazol-2-yl]amino]pentanedioate	HCID 178471552	—
Reactant	2-(methylamino)-5-[[4-(4-oxopiperidin-1-yl)phenyl]methylidene]-1,3-thiazol-4-one	HCID 178482435	—
Product	HCID 178525470	HCID 178525470	—

Reaction Steps

The title compound was prepared from (2S)-2-{5-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzylidene]-4-oxo-4,5-dihydro-thiazol-2-ylamino}-pentanedioic acid diethyl ester (which was obtained in Intermediate 34) and (S)-4-[2-hydroxy-3-aminopropoxy]-1,3-dihydro-2H-benzimidazol-2-one (Jesudason, C. D., et al., EP 0 764 640) according to the procedures of Intermediate 18, Example 1 and Example 9 as a yellowish solid; mp>270° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ 1.40-1.70 (m, 2 H), 1.80-4.30 (m, 17 H), 6.50-6.80(m, 2 H), 6.80-7.10(m, 3 H), 7.23(d, J=8.4 Hz, 2 H), 7.37 (s, 1 H), 10.61(brs, 1 H), 11.01 (brs, 1 H); MS (ES) m/z: 320.3 ((M+2H)2+, 100%); 639.4 (MH+, 60%); HRMS Calcd. for C30H35N6O8S (MH+): 639.2231. Found: 639.2233.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06821991B2
Source dataset	uspto-grants-2004_11
ORD ID	ord-607f04d2f2b64a3fb23fcb15de86b4b1
Source note	uspto-grants-2004_11