N-[5-((2S)-3-Amino-2-hydroxy-propoxy)-2-hydroxy-phenyl]-methanesulfonamide → N-(4-{4-[((2S)-2-Hydroxy-3-{4-hydroxy-3-[(methylsulfonyl)amino]phenoxy}-propyl)amino]-1-piperidineyl}phenyl)-1-butanesulfonamide

HRID 1061395Notes

Reaction equation

HRID 1061395 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH2:18][CH2:19][CH2:20][CH3:21])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:22][CH2:23][C@H:24]([OH:39])[CH2:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([OH:38])=[C:31]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:32]=1>>[OH:39][C@H:24]([CH2:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([OH:38])=[C:31]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:32]=1)[CH2:23][NH:22][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([CH2:18][CH2:19][CH2:20][CH3:21])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 69655007N-[5-((2S)-3-Amino-2-hydroxy-propoxy)-2-hydroxy-phenyl]-methanesulfonamideHCID 86584570N-[4-(4-Oxo-1-piperidinyl)phenyl]-1-butanesulfonamide

Product 1

HCID 69654649N-(4-{4-[((2S)-2-Hydroxy-3-{4-hydroxy-3-[(methylsulfonyl)amino]phenoxy}-propyl)amino]-1-piperidineyl}phenyl)-1-butanesulfonamide

Procedure

The title compound was prepared from butane-1-sulfonic acid [4-(4-oxo-piperidine-1-yl)-phenyl]-amide (which was obtained in Example 228) and N-[5-((2S)-3-amino-2-hydroxy-propoxy)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 14) according to the procedure of Example 278 as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.83 (t, J=7.3 Hz, 3H), 1.25-1.40 (m, 2H), 1.55-1.70 (m, 2H), 1.80-1.95 (m, 2H), 2.50-2.80 (m, 5H), 2.92 (s, 3H), 2.85-3.30 (m, 2H), 3.50-3.65 (m, 2H), 3.70-3.90 (m, 3H), 6.61 (dd, J=8.8, 2.9 Hz, 1H), 6.70-6.80 (m, 2H), 6.88 (d, J=8.9 Hz, 2H), 7.05 (d, J=8.9 Hz, 2H); MS (ES) m/z: 571.0 (MH+); HRMS Calcd. for C25H39N4O7S2 (MH+): 571.2261. Found: 571.2279.

Sources & evidence

ORD record
ord-b7d8052476c94fbca26d88bf91a1f9c5
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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