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-butanesulfonamide

HRID 1061383Notes

Reaction equation

HRID 1061383 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.C([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH:36]([OH:53])[CH2:37][N:38](CC2C=CC=CC=2)CC2C=CC=CC=2)=[CH:32][C:31]=1[NH:54][S:55]([CH3:58])(=[O:57])=[O:56])C1C=CC=CC=1>>[OH:53][CH:36]([C:33]1[CH:34]=[CH:35][C:30]([OH:29])=[C:31]([NH:54][S:55]([CH3:58])(=[O:57])=[O:56])[CH:32]=1)[CH2:37][NH:38][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 22220247N-[2-Benzyloxy-5-(2-dibenzylamino-1-hydroxy-ethyl)-phenyl]-methanesulfonamideHCID 86584570N-[4-(4-Oxo-1-piperidinyl)phenyl]-1-butanesulfonamide

Product 1

HCID 22220271N-(4-{4-[(2-Hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]phenyl}ethyl)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-[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 0.83 (t, J=7.2 Hz, 3H), 1.20-1.40 (m, 2H), 1.50-1.70 (m, 4H), 1.95-2.10 (m, 2H), 2.40-2.60 (m, 2H), 2.94 (s, 3H), 2.90-3.20 (m, 5H), 3.62-3.75 (m, 2H), 4.70-4.80 (m, 1H), 5.95 (brs, 1H), 6.85-6.95 (m, 3H), 7.00-7.10 (m, 3H), 7.24 (d, J=2.0 Hz, 1H), 8.70 (brs, 1H), 9.33 (brs, 1H); MS (ES) m/z: 541.0 (MH+); HRMS Calcd. for C24H37N4O6S2 (MH+): 541.2155. Found: 541.2161.

Sources & evidence

ORD record
ord-d7be87d5e43f476d8d1ca16950f6634b
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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