(+)-Norepinephrine → N-(4-{[2-(4-{[(2R)-2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]amino}-1-piperidinyl)-anilino]sulfonyl}phenyl)acetamide

HRID 1061366Notes

Reaction equation

HRID 1061366 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[C:33]([C@H:34]([OH:37])[CH2:35][NH2:36])=[CH:32][C:31]([OH:38])=[C:30]([OH:39])[CH:29]=1>>[OH:38][C:31]1[CH:32]=[C:33]([C@@H:34]([OH:37])[CH2:35][NH:36][CH:2]2[CH2:3][CH2:4][N:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[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:16])=[O:17])[CH2:6][CH2:7]2)[CH:28]=[CH:29][C:30]=1[OH:39]

Participants

3

Reactant 2

HCID 5814(+)-NorepinephrineHCID 69654669N-{4-[2-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide

Product 1

HCID 69654757N-(4-{[2-(4-{[(2R)-2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]amino}-1-piperidinyl)-anilino]sulfonyl}phenyl)acetamide

Procedure

The title compound was prepared from N-{4-[2-(4-oxo-piperidine-1-yl)-phenylsulfamoyl]-phenyl}-acetamide (which was obtained in Example 222) and L-norepinephrine according to the procedure of Example 255 as a grey solid; 1H NMR (300 MHz, DMSO-d6) δ 1.30-1.52 (m, 2H), 1.70-1.90 (m, 2H), 1.89 (s, 3H), 2.50-3.50 (m, 7H), 4.40-4.55 (m, 1H), 6.00 (brs, 1H), 6.50-6.80 (m, 3H), 6.95-7.15 (m, 2H), 7.25-7.40 (m, 2H), 7.60-7.75 (m, 4H), 10.30 (s, 1H); MS (ES) m/z: 541.4 (MH+); HRMS Calcd. for C27H33N4O6S(MH+): 541.2121. Found: 541.2110.

Sources & evidence

ORD record
ord-41e363b7c7f04617925a103a17a77b36
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

Loading…