{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenoxy}-acetic acid methyl ester → Methyl{4-[(4-{4-[((2r)-2-{4-chloro-3-[(methylsulfonyl)amino]phenyl}-2-hydroxyethyl)amino]-1-piperidineyl}anilino)sulfonyl]phenoxy}acetate
Reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:28])(=[O:27])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.[N:30]([CH2:33][C@@H:34]([C:36]1[CH:37]=[CH:38][C:39]([Cl:47])=[C:40]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])[CH:41]=1)[OH:35])=[N+]=[N-]>>[CH3:1][O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:21][CH2:22][CH:23]([NH:30][CH2:33][C@@H:34]([C:36]4[CH:37]=[CH:38][C:39]([Cl:47])=[C:40]([NH:42][S:43]([CH3:46])(=[O:44])=[O:45])[CH:41]=4)[OH:35])[CH2:24][CH2:25]3)=[CH:18][CH:19]=2)(=[O:27])=[O:28])=[CH:10][CH:11]=1Participants
Procedure
The title compound was prepared from {4-[4-(4-oxo-piperidine-1-yl)-phenylsulfamoyl]-phenoxy}-acetic acid methyl ester (which was obtained in Example 232) and N-[5-((1R)-2-azido-1-hydroxy-ethyl)-2-chloro-phenyl]-methanesulfonamide (which was obtained in Example 25) according to the procedure of Example 95 as a pale grey solid; 1H NMR (300 MHz, DMSO-d6) δ 1.20-1.40 (m, 2H), 1.75-1.90 (m, 2H), 2.50-2.80 (m, 5H), 2.97 (s, 3H), 3.40-3.55 (m, 2H), 3.69 (s, 3H), 4.63 (dd, J=8.0, 3.8 Hz, 1H), 4.87 (s, 2H), 6.77 (d, J=9.0 Hz, 2H), 6.87 (d, J=9.0Hz, 2H), 7.03 (d, J=9.0Hz, 2H), 7.17 (dd, J=8.3, 1.7 Hz, 1H), 7.43 (d, J=8.3 Hz, 1H), 7.43 (d, J=1.7 Hz, 1H), 7.62 (d, J=9.0 Hz, 2H); MS (ES) m/z: 667.0 (MH+); HRMS Calcd. for C29H36ClN4O8S2 (MH+): 667.1657. Found: 667.1651.
Sources & evidence
- ORD record
- ord-6ad091aff2e74d7288a4b49948df38fd
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06525202B2
Reaction notes
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