N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide → HCID 10210215, compound

HRID 1061314Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:25])[C:5](=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]2)=[CH:14][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[NH2:26][CH2:27][CH:28]([C:30]1[CH:31]=[CH:32][C:33]([OH:41])=[C:34]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:35]=1)[OH:29]>>[CH2:1]([O:3][C:4](=[O:25])[C:5](=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:19][CH2:20][CH:21]([NH:26][CH2:27][CH:28]([OH:29])[C:30]3[CH:31]=[CH:32][C:33]([OH:41])=[C:34]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:35]=3)[CH2:22][CH2:23]2)=[CH:14][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

Reactant 2

HCID 9837752N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide

HCID 69654958HCID 69654958, compound

Product 1

HCID 10210215HCID 10210215, compound

Procedure

The title compound was prepared from 2-[4-(4-oxo-piperidine-1-yl)-benzylidene]-malonic acid diethyl ester (which was obtained in Example 153) and N-[5-(-2-amino-1-hydroxy- ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 9) according to the procedure of Example 180 as a yellowish solid; mp >80° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.21 (t, J=7.0 Hz, 3H), 1.23 (t, J=7.0 Hz, 3H), 1.75-1.95 (m, 2H), 2.50-3.50 (m, 7H), 2.92 (s, 3H), 3.75-3.90 (m, 2H), 4.21 (q, J=7.0 Hz, 2H), 4.31 (q, J=7.0 Hz, 2H), 4.47 (dd, J=8.0, 4.2 Hz, 1H), 6.81 (d, J=8.2 Hz, 1H), 6.94 (d, J=9.0 Hz, 2H), 7.00 (dd, J=8.2, 2.0 Hz, 1H), 7.17 (d, J=2.0 Hz, 1H), 7.33 (d, J=9.0 Hz, 2H), 7.52 (s, 1H); MS (ES) m/z: 576.1 (MH+); HRMS Calcd. for C28H38N3O8S(MH+): 576.2374. Found: 576.2375.

Sources & evidence

ORD record: ord-2d6b5103831e46c991ba613ab6962e80
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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