N-[2-Benzyloxy-5-(2-dibenzylamino-1-hydroxy-ethyl)-phenyl]-methanesulfonamide → N-(4-{4-[(2-Hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidineyl}phenyl)-1-octanesulfonamide

HRID 1061385Notes

Reaction equation

HRID 1061385 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][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C([O:33][C:34]1[CH:39]=[CH:38][C:37]([CH:40]([OH:57])[CH2:41][N:42](CC2C=CC=CC=2)CC2C=CC=CC=2)=[CH:36][C:35]=1[NH:58][S:59]([CH3:62])(=[O:61])=[O:60])C1C=CC=CC=1>>[OH:57][CH:40]([C:37]1[CH:38]=[CH:39][C:34]([OH:33])=[C:35]([NH:58][S:59]([CH3:62])(=[O:61])=[O:60])[CH:36]=1)[CH2:41][NH:42][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][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 22220247N-[2-Benzyloxy-5-(2-dibenzylamino-1-hydroxy-ethyl)-phenyl]-methanesulfonamideHCID 86584572Octane-1-sulfonic acid [4-(4-oxo-1-piperidineyl)-phenyl]-amide

Product 1

HCID 22220334N-(4-{4-[(2-Hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)amino]-1-piperidineyl}phenyl)-1-octanesulfonamide

Procedure

The title compound was prepared from octane-1-sulfonic acid [4-(4-oxo-piperidine-1-yl)-phenyl]-amide (which was obtained in Example 230) and N-[2-benzyloxy-5-(2-dibenzylamino-1-hydroxy-ethyl)-phenyl]-methanesulfonamide (which was obtained in Example 7) according to the procedure of Example 255 as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.84 (t, J=7.0 Hz, 3H), 1.15-1.40 (m, 12H), 1.50-1.70 (m, 2H), 1.80-1.95 (m, 2H), 2.50-2.92 (m, 7H), 3.50-3.65 (m, 2H), 4.49 (dd, J=8.0, 4.1 Hz, 1H), 6.82 (d, J=8.3 Hz, 1H), 6.88 (d, J=8.0 Hz, 2H), 7.00 (dd, J=8.3, 2.0 Hz, 1H), 7.04 (d, J=8.0 Hz, 2H), 7.17 (d, J=2.0 Hz, 1H); MS (ES) m/z: 597.1 (MH+); HRMS Calcd. for C28H45N4O6S2 (MH+): 597.2781. Found: 597.2776.

Sources & evidence

ORD record
ord-d38be6e26ff34814bedff5ad052dbabb
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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