N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamide → HCID 69655031, compound

HRID 1061250Notes

Reaction equation

HRID 1061250 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:21]=[CH:20][C:11]([CH2:12][CH:13]3[NH:17][C:16](=[O:18])[NH:15][C:14]3=[O:19])=[CH:10][CH:9]=2)[CH2:4][CH2:3]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]>>[O:18]=[C:16]1[NH:17][CH:13]([CH2:12][C:11]2[CH:20]=[CH:21][C:8]([N:5]3[CH2:6][CH2:7][CH:2]([NH:22][CH2:23][CH:24]([C:26]4[CH:27]=[CH:28][C:29]([OH:37])=[C:30]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH:31]=4)[OH:25])[CH2:3][CH2:4]3)=[CH:9][CH:10]=2)[C:14](=[O:19])[NH:15]1

Participants

3

Reactant 2

HCID 9837752N-[5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl]methanesulphonamideHCID 12965958HCID 12965958, compound

Product 1

HCID 69655031HCID 69655031, compound

Procedure

The title compound was prepared from 5-[4-(4-oxo-piperidine-1-yl)-benzyl]-imidazolidine-2,4-dione (which was obtained in Example 44) 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 >105° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.40 (m, 2H), 1.80-2.00 (m, 2H), 2.50-2.75 (m, 5H), 2.86 (d, J=4.8 Hz, 2H), 2.93 (s, 3H), 3.50-3.65 (m, 2H), 4.24 (t, J=4.8 Hz, 1H), 4.51 (dd, J=8.2, 4.0 Hz, 1H), 6.81 (d, J=6.3 Hz, 1H), 6.84 (d, J=5.7 Hz, 2H), 7.18 (d, J=1.8 Hz, 1H), 7.85 (brs, 1H); MS (ES) m/z: 518.0 (MH+); HRMS Calcd. for C24H32N5O6S(MH+): 518.2073. Found: 518.2056.

Sources & evidence

ORD record
ord-696e380dec844a5eb9509c15206a54bf
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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