(+-)-Normetanephrine → HCID 22220574, compound

HRID 1061368Notes

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.[CH3:28][O:29][C:30]1[CH:35]=[C:34]([CH:36]([OH:39])[CH2:37][NH2:38])[CH:33]=[CH:32][C:31]=1[OH:40]>>[OH:39][CH:36]([C:34]1[CH:33]=[CH:32][C:31]([OH:40])=[C:30]([O:29][CH3:28])[CH:35]=1)[CH2:37][NH:38][CH:2]1[CH2:3][CH2:4][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:17])=[O:16])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

Reactant 2

HCID 1237(+-)-Normetanephrine

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

Product 1

HCID 22220574HCID 22220574, compound

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 DL-normetanephrine according to the procedure of Example 255 as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.40-1.60 (m, 2H), 1.90-2.06 (m, 2H), 2.06 (s, 3H), 2.50-3.50 (m, 5H), 3.55-3.65 (m, 2H), 3.77 (s, 3H), 4.70-4.80 (m, 1H), 5.70-5.85 (brs, 1H), 6.70-6.90 (m, 7H), 7.59 (d, J=8.7 Hz, 2H), 7.69 (d, J=8.7 Hz, 2H), 8.95 (brs, 1H), 10.37 (s, 1H); MS (ES) m/z: 555.2 (MH+); HRMS Calcd. for C28H35N4O6S(MH+): 555.2277. Found: 555.2265.

Sources & evidence

ORD record: ord-543b3a31d18448488687d8b0a9d61584
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525202B2

Reaction notes

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