N-{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide → N-{4-[(4-{4-[((2R)-2-Hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]-phenyl}ethyl)amino]-1-piperidineyl}anilino)sulfonyl]phenyl}acetamide

HRID 1061380Notes

Reaction equation

HRID 1061380 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]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C([O:35][C:36]1[CH:41]=[CH:40][C:39]([C@@H:42]([OH:45])[CH2:43][NH2:44])=[CH:38][C:37]=1[NH:46][S:47]([CH3:50])(=[O:49])=[O:48])C1C=CC=CC=1>>[OH:45][C@H:42]([C:39]1[CH:40]=[CH:41][C:36]([OH:35])=[C:37]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[CH:38]=1)[CH2:43][NH:44][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=3)(=[O:16])=[O:17])=[CH:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 22220411N-{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamideHCID 69654885N-[2-Benzyloxy-5-(2-amino-(1R)-1-hydroxy-ethyl)-phenyl]-methanesulfonamide

Product 1

HCID 69654848N-{4-[(4-{4-[((2R)-2-Hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]-phenyl}ethyl)amino]-1-piperidineyl}anilino)sulfonyl]phenyl}acetamide

Procedure

The title compound was prepared from N-{4-[4-(4-oxo-piperidine-1-yl)-phenylsulfamoyl]-phenyl}-acetamide (which was obtained in Example 216) and N-[5-((1R)-2-amino-1-hydroxy-ethyl)-2-benzyloxy-phenyl]-methanesulfonamide (which was obtained in Example 8) according to the procedure of Example 255 as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.40-1.70 (m, 2H), 1.90-2.10 (m, 2H), 2.06 (s, 3H), 2.50-2.65 (m, 2H), 2.90-3.15 (m, 3H), 2.94 (s, 3H), 3.55-3.70 (m, 2H), 4.65-4.80 (m, 1H), 6.79 (d, J=9.0 Hz, 2H), 6.97 (d, J=9.0 Hz, 2H), 7.00 (d, J=8.0 Hz, 1H), 7.06 (dd, J=8.0, 1.2 Hz, 1H), 7.22 (d, J=1.2 Hz, 1H), 7.40 (d, J=8.7 Hz, 2H), 7.69 (d, J=8.7 Hz, 2H), 10.42 (s, 1H), 10.44 (s, 1H); MS (ES) m/z: 618.0 (MH+); HRMS Calcd. for C28H36N5O7S2 (MH+): 618.2056. Found: 618.2056.

Sources & evidence

ORD record
ord-0ecb71d311aa43edb9eaf1965255cfc6
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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