N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide → HCID 178505036, compound

HRID 1370209Notes

Reaction equation

HRID 1370209 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[S:16][C:17](=[CH:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]4)=[CH:24][CH:23]=3)[C:18](=[O:20])[N:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:35][CH2:36][CH:37]([C:39]1[CH:40]=[CH:41][C:42]([OH:50])=[C:43]([NH:45][S:46]([CH3:49])(=[O:48])=[O:47])[CH:44]=1)[OH:38]>>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[S:16][C:17](=[CH:21][C:22]3[CH:23]=[CH:24][C:25]([N:28]4[CH2:29][CH2:30][CH:31]([NH:35][CH2:36][CH:37]([C:39]5[CH:40]=[CH:41][C:42]([OH:50])=[C:43]([NH:45][S:46]([CH3:49])(=[O:48])=[O:47])[CH:44]=5)[OH:38])[CH2:32][CH2:33]4)=[CH:26][CH:27]=3)[C:18](=[O:20])[N:19]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 9837752N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide2×HCID 178516398HCID 178516398, compound2×

Product 1

HCID 178505036HCID 178505036, compound

Procedure

The title compound was prepared from 1-{4-[2-(1-benzyl-piperdin-4-ylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-phenyl}-piperidin-4-one (which was obtained in Intermediate 21) and N-[5-(2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Intermediate 9) according to the procedure of Example 1 as a pale yellowish solid; mp >210° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.40 (m, 2 H), 1.40-1.65 (m, 2 H), 1.70-2.00 (m, 4 H), 2.06 (brt, J=9.8 Hz, 2 H), 2.50-3.50 (m, 6 H), 2.92 (s, 3 H), 3.47 (s, 2 H), 3.70-4.00 (m, 2 H), 4.47 (dd, J=7.9, 4.3 Hz, 1 H), 6.81 (d, J=8.2 Hz, 1 H), 6.95-7.05 (m, 2 H), 7.17 (d, J=1.9 Hz, 1 H), 7.20-7.55 (m, 8H); MS (ES) m/z:353.1 ((M+2 H)2+, 100%); 705.1 (MH+, 5%); HRMS Calcd. for C36H45N6O5S2 (MH+): 705.2893. Found: 705.2921.

Sources & evidence

ORD record
ord-e41e41e1d0e24faba342e9b289cd14ff
Source dataset
uspto-grants-2003_06
Patent number
US06583140B2

Reaction notes

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