Norfenefrine → N-[4-(4-{4-[2-Hydroxy-2-(3-hydroxy-phenyl)-ethylamino]-piperidin-1-yl}-Phenylsulfamovl)-phenyl]-acetamide

HRID 1794864Notes

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.[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][C:11]([NH:14][S:15]([C:18]3[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:22][CH:23]=3)(=[O:16])=[O:17])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

Reactant 2

HCID 4538Norfenefrine

HCID 22220411N-{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide

Product 1

HCID 22220518N-[4-(4-{4-[2-Hydroxy-2-(3-hydroxy-phenyl)-ethylamino]-piperidin-1-yl}-Phenylsulfamovl)-phenyl]-acetamide

Procedure

The title compound was prepared from N-{4-[4-(4-oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide (which was obtained in Example 216) and DL-norphenylephrine according to the procedure of Example 255 as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.35–1.50 (m, 2 H), 1.80–2.00 (m, 2 H), 2.06 (s, 3 H), 2.50–2.90 (m, 5 H), 3.45–3.60 (m, 2 H), 4.55–4.65 (m, 1 H), 5.55 (brs, 1 H), 6.60–6.70 (m, 1 H), 6.70–6.85 (m, 4 H), 6.86 (d, J=9.3 Hz, 2 H), 7.11 (t, J=7.8 Hz, 1 H), 7.58 (d, J=8.7 Hz, 2 H), 7.68 (d, J=8.7 Hz, 2 H), 9.35 (s, 1 H), 10.33 (s, 1 H); MS (ES) m/z: 525.4 (MH+); HRMS Calcd. for C27H33N4O5S (MH+): 525.2172. Found: 525.2177.

Sources & evidence

ORD record: ord-328cbcabedff431ab02bf28deb8b7b4f
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022716B2

Reaction notes

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