(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide → HCID 9803765, compound

HRID 1794818Notes

Reaction equation

HRID 1794818 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:17][CH2:18][C@@H:19]([C:21]1[CH:22]=[CH:23][C:24]([OH:32])=[C:25]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:26]=1)[OH:20]>>[OH:20][C@H:19]([C:21]1[CH:22]=[CH:23][C:24]([OH:32])=[C:25]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH:26]=1)[CH2:18][NH:17][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 220640224-(4-Oxopiperidin-1-yl)benzoic acid

Product 1

HCID 9803765HCID 9803765, compound

Procedure

The title compound was prepared from 4-(4-oxo-piperidin-1-yl)-benzoic acid (which was obtained in Example 151) and N-[5-((1R)-2-amino-1-hydroxy-ethyl)-2-hydroxy-phenyl]-methanesulfonamide (which was obtained in Example 10) according to the procedure of Example 179 as a white solid; mp>85° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.20–1.40 (m, 2 H), 1.80–1.95 (m, 2 H), 2.60–3.00 (m, 5 H), 2.92 (s, 3 H), 3.75–3.85 (m, 2 H), 4.53 (dd, J=8.3, 4.0 Hz, 1 H), 6.82 (d, J=8.3 Hz, 1 H), 6.92 (d, J=8.9 Hz, 2 H), 7.01 (dd, J=8.3, 2.0 Hz, 1 H), 7.19 (d, J=2.0 Hz, 1 H), 7.73 (d, J=8.9 Hz, 2 H); MS (ES) m/z: 449.9 (MH+); HRMS Calcd. for C21H26N3O6S(M−H)−: 448.1549: Found: 448.1541.

Sources & evidence

ORD record
ord-023c6b8b690a47aebb2742f08035e382
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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