N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide → HCID 145832533, compound

HRID 1794756Notes

Reaction equation

[NH:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][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]([CH2:8][CH: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 145832527HCID 145832527, compound

Product 1

HCID 145832533HCID 145832533, compound

Procedure

The title compound was prepared from 1-[4-(2-imino-4-oxo-thiazolidin-5-ylmethyl)-phenyl]-piperidin-4-one (which was obtained in Example 45) and N-[5–2-amino-1hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 9) according to the procedure of Example 73 as a pale yellowish solid; mp>90° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.20–1.40 (m, 2 H), 1.80–2.00 (m, 2 H), 2.50–2.80 (m, 6 H), 2.93 (s, 3 H), 3.25 (dd, J=14.2, 3.9 Hz, 1 H), 3.45–3.60 (m, 2 H), 4.40–4.55 (m, 2 H), 6.81 (d, J=8.3 Hz, 1 H), 6.88 (d, J=8.6 Hz, 2 H), 6.96 (dd, J=8.3, 2.0 Hz, 1 H), 7.04 (d, J=8.6 Hz, 2 H), 7.16 (d, J=2.0 Hz, 1 H); MS (ES) m/z: 267.7 ((M+2H)2+100%), 534.3 (MH+, 45%), 1067.0 (2MH+, 2%); HRMS Calcd. for C24H32N5O5S2 (MH+): 534.1845. Found: 534.1850.

Sources & evidence

ORD record: ord-e4ee966b2b2746f08633dcb1b2a95b86
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022716B2

Reaction notes

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