(R)-Octopamine → HCID 22220447, compound

HRID 1794866Notes

Reaction equation

HRID 1794866 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[C:33]([C@@H:34]([OH:37])[CH2:35][NH2:36])=[CH:32][CH:31]=[C:30]([OH:38])[CH:29]=1>>[OH:37][CH:34]([C:33]1[CH:32]=[CH:31][C:30]([OH:38])=[CH:29][CH:28]=1)[CH2:35][NH:36][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][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:12][CH:13]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 440266(R)-OctopamineHCID 22220411N-{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide

Product 1

HCID 22220447HCID 22220447, compound

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-octopamine according to the procedure of Example 255 as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.55–1.75 (m, 2 H), 2.00–2.15 (m, 2 H), 2.06 (s, 3 H), 2.50–3.20 (m, 5 H), 3.60–3.70 (m, 2 H), 4.80–4.90 (m, 1 H), 6.00 (brs, 1 H), 6.76 (d, J=9.7 Hz, 2 H), 6.80 (d, J=9.7 Hz, 2 H), 6.88 (d, J=9.0 Hz, 2 H), 7.19 (d, J=8.7 Hz, 2 H), 7.59 (d, J=9.0 Hz, 2 H), 7.70 (d, J=8.7 Hz, 2 H), 9.47 (s, 1 H), 10.43 (s, 1 H); MS (ES) m/z: 525.3 (MH+); HRMS Calcd. for C27H33N4O5S (MH+): 525.2172. Found: 525.2178.

Sources & evidence

ORD record
ord-d73e40827b1e4461a5647bdf60a06c62
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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