(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → Methyl{4-[(4-{4-[((2r)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]-phenyl}ethyl)amino]-1piperidinyl}anilino)sulfonyl]phenoxy}acetate

HRID 1061397Notes

Reaction equation

HRID 1061397 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.[NH2:30][CH2:31][C@@H:32]([C:34]1[CH:35]=[CH:36][C:37]([OH:45])=[C:38]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[CH:39]=1)[OH:33]>>[CH3:1][O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][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][CH2:31][C@H:32]([OH:33])[C:34]4[CH:35]=[CH:36][C:37]([OH:45])=[C:38]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[CH:39]=4)[CH2:24][CH2:25]3)=[CH:18][CH:19]=2)(=[O:28])=[O:27])=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 69654907{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenoxy}-acetic acid methyl ester

Product 1

HCID 91381200Methyl{4-[(4-{4-[((2r)-2-hydroxy-2-{4-hydroxy-3-[(methylsulfonyl)amino]-phenyl}ethyl)amino]-1piperidinyl}anilino)sulfonyl]phenoxy}acetate

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-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 10) according to the procedure of Example 278 as an off-white 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), 2.92 (s, 3H), 3.65-3.75 (m, 2H), 3.67 (s, 3H), 4.47 (dd, J=8.0, 4.1 Hz, 1H), 4.87 (s, 2H), 6.50-6.90 (m, 8H), 7.17 (d, J=1.8 Hz, 1H), 7.59 (d, J=8.9 Hz, 2H); MS (ES) m/z: 649.0 (MH+); HRMS Calcd. for C29H37N4O9S2 (MH+): 649.2004. Found: 649.2014.

Sources & evidence

ORD record
ord-76d799ceb2c84f7b82c64bca84ebe2e5
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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