N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide → HCID 145832529, compound

HRID 1794754Notes

Reaction equation

[NH:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4](=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[S:3]1.[NH2:22][CH2:23][CH:24]([C:26]1[CH:27]=[CH:28][C:29]([OH:37])=[C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:31]=1)[OH:25]>>[OH:37][C:29]1[CH:28]=[CH:27][C:26]([CH:24]([OH:25])[CH2:23][NH:22][CH:18]2[CH2:19][CH2:20][N:15]([C:12]3[CH:13]=[CH:14][C:9]([CH:8]=[C:4]4[S:3][C:2](=[NH:1])[NH:6][C:5]4=[O:7])=[CH:10][CH:11]=3)[CH2:16][CH2:17]2)=[CH:31][C:30]=1[NH:32][S:33]([CH3:36])(=[O:35])=[O:34]

Participants

Reactant 2

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

HCID 152746543HCID 152746543, compound

Product 1

HCID 145832529HCID 145832529, compound

Procedure

The title compound was prepared from 1-[4-(2-imino-4-oxo-thiazolidin-5-ylidenemethyl)-phenyl]-piperidin-4-one (which was obtained in Example 43) and N-[5-(2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 9) according to the procedure of Example 73 as a pale yellowish solid; mp>210° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.20–1.40 (m, 2 H), 1.80–2.00 (m, 2 H), 2.50–3.00 (m, 5 H), 2.92 (s, 3 H), 3.70–3.90 (m, 2 H), 4.47 (dd, J=7.9, 4.4 Hz, 1 H), 6.81 (d,J=8.3 Hz, 1 H), 6.90–7.10 (m, 3 H), 7.18 (d, J=2.0 Hz, 2 H), 7.39 (d, J=8.9 Hz, 2 H), 7.47 (s, 1 H); MS (ES) m/z: 532.0 (MH+); HRMS Calcd. for C24H30N5O5S2 (MH+): 532.1688. Found: 532.1672.

Sources & evidence

ORD record: ord-5c2669423b814b33bff135f51162837d
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022716B2

Reaction notes

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