Norfenefrine → n-(4-{[2-(4-{[2-Hydroxy-2-(3-hydroxyphenyl)ethyl]amino}-1-piperidineyl)anilino]-sulfonyl}phenyl)acetamide

HRID 1794871Notes

Reaction equation

HRID 1794871 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:4][CH2:3]1.[CH:28]1[CH:33]=[C:32]([OH:34])[CH:31]=[C:30]([CH:35]([OH:38])[CH2:36][NH2:37])[CH:29]=1>>[OH:38][CH:35]([C:30]1[CH:29]=[CH:28][CH:33]=[C:32]([OH:34])[CH:31]=1)[CH2:36][NH:37][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 4538NorfenefrineHCID 69654669N-{4-[2-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide

Product 1

HCID 22220398n-(4-{[2-(4-{[2-Hydroxy-2-(3-hydroxyphenyl)ethyl]amino}-1-piperidineyl)anilino]-sulfonyl}phenyl)acetamide

Procedure

The title compound was prepared from N-{4-[2-(4-oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide (which was obtained in Example 222) and DL-norphenylephrine according to the procedure of Example 255 as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.70–1.90 (m, 2 H), 1.90–2.10 (m, 2 H), 2.06 (s, 3 H), 2.50–3.20 (m, 7 H), 4.75–4.95 (m, 1 H), 6.10 (brs, 1 H), 6.50–7.40 (m, 8 H), 7.65–7.80 (m, 4 H), 9.48 (s, 1 H), 10.42 (s, 1 H); MS (ES) m/z: 525.6 (MH+); HRMS Calcd. for C27H33N4O5S (MH+): 525.2172. Found: 525.2164.

Sources & evidence

ORD record
ord-156fc8505ba44c2f8da71548a3215942
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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