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

HRID 2416079Notes

Reaction equation

HRID 2416079 reaction equation
C([O:3][C:4](=[O:37])[C@@H:5]([NH:13][C:14]1[S:15][C:16](=[CH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:36][CH2:35][C:30]4(OCCO4)[CH2:29][CH2:28]3)=[CH:23][CH:22]=2)[C:17](=[O:19])[N:18]=1)[CH2:6][CH2:7][C:8]([O:10]CC)=[O:9])C.[OH:38][C@@H:39]([CH2:52][NH2:53])[CH2:40][O:41][C:42]1[C:50]2[NH:49][C:48](=[O:51])[NH:47][C:46]=2[CH:45]=[CH:44][CH:43]=1.CNC1SC(=CC2C=CC(N3CCC(=O)CC3)=CC=2)C(=O)N=1.NCC(C1C=CC(O)=C(NS(C)(=O)=O)C=1)O>>[OH:38][C@H:39]([CH2:40][O:41][C:42]1[C:50]2[NH:49][C:48](=[O:51])[NH:47][C:46]=2[CH:45]=[CH:44][CH:43]=1)[CH2:52][NH:53][CH:30]1[CH2:29][CH2:28][N:27]([C:24]2[CH:25]=[CH:26][C:21]([CH:20]=[C:16]3[S:15][C:14]([NH:13][C@@H:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[C:4]([OH:3])=[O:37])=[N:18][C:17]3=[O:19])=[CH:22][CH:23]=2)[CH2:36][CH2:35]1

Participants

5

Reactant 4

HCID 9837752N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamideHCID 107991054-((2S)-3-Amino-2-hydroxy-propoxy)-1,3-dihydrobenzoimidazol-2-oneHCID 178471552diethyl (2S)-2-[[5-[[4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)phenyl]methylidene]-4-oxo-1,3-thiazol-2-yl]amino]pentanedioate2×HCID 1784824352-(methylamino)-5-[[4-(4-oxopiperidin-1-yl)phenyl]methylidene]-1,3-thiazol-4-one

Product 1

HCID 178525470HCID 178525470, compound

Procedure

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.

Sources & evidence

ORD record
ord-607f04d2f2b64a3fb23fcb15de86b4b1
Source dataset
uspto-grants-2004_11
Patent number
US06821991B2

Reaction notes

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