HCID 10751302, compound → 4-[4-[[(2R)-2-Hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-1-piperidinyl]benzamide

HRID 1061315Notes

Reaction equation

HRID 1061315 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[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]([NH2:14])=[O:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 10751302HCID 10751302, compoundHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide

Product 1

HCID 105754554-[4-[[(2R)-2-Hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-1-piperidinyl]benzamide

Procedure

The title compound was prepared from 4-(4-oxo-piperidine-1-yl)-benzamide (which was obtained in Example 147) 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 180 as a white solid; mp >75° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.2-1.40 (m, 2H), 1.70-1.90 (m, 2H), 2.55-2.95 (m, 5H), 2.97 (s, 3H), 3.70-3.85 (m, 2H), 4.48 (dd, J=8.0, 4.3 Hz, 1H), 6.81 (d, J=8.2 Hz, 1H), 6.91 (d, J=9.0 Hz, 2H), 6.99 (dd, J=8.2, 2.0 Hz, 1H), 7.17 (d, J=2.0 Hz, 1H), 7.67 (br s, 2H), 7.72 (d, J=9.0 Hz, 2H); MS (ES) m/z: 448.9 (MH+); HRMS Calcd. for C21H29N4O5S(MH+): 449.1853. Found: 449.1853.

Sources & evidence

ORD record
ord-08859974003c4b6b976c7e1e4655ea10
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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