1-Amino-3-(4-methoxyphenoxy)propan-2-ol → N-(4-{[4-(4-{[2-Hydroxy-3-(4-methoxyphenoxy)propyl]amino}-1-pieridinyl)anilino]-sulfonyl}phenyl)acetamide

HRID 1061364Notes

Reaction equation

HRID 1061364 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.[NH2:28][CH2:29][CH:30]([OH:41])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1>>[OH:41][CH:30]([CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)[CH2:29][NH:28][CH:2]1[CH2:3][CH2:4][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)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 27353601-Amino-3-(4-methoxyphenoxy)propan-2-olHCID 22220411N-{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide

Product 1

HCID 22220534N-(4-{[4-(4-{[2-Hydroxy-3-(4-methoxyphenoxy)propyl]amino}-1-pieridinyl)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 1-amino-3-(4-methoxy-phenoxy)-propan-2-ol according to the procedure of Example 255 as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.55-1.75 (m, 2H), 1.95-2.15 (m, 2H), 2.06 (s, 3H), 2.50-3.20 (m, 5H), 3.85-3.95 (m, 2H), 4.10-4.20 (m, 1H), 5.70 (brs, 1H), 6.80 (d, J=9.0 Hz, 2H), 6.80-6.95 (m, 6H), 7.59 (d, J=9.0 Hz, 2H), 7.69 (d, J=9.0 Hz, 2H), 10.38 (s, 1H); MS (ES) m/z: 569.6 (MH+); HRMS Calcd. for C29H37N4O6S(MH+): 569.2434. Found: 569.2418.

Sources & evidence

ORD record
ord-28cd6dc819b54829abe03b52764c170b
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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