(2S)-(-)-1-Amino-3-phenoxy-2-propanol → N-(4-{[4-(4-{[(2S)-2-Hydroxy-3-phenoxypropyl]amino}-1-piperidineyl)anilino]-sulfonyl}phenyl)acetamide

HRID 1061373Notes

Reaction equation

HRID 1061373 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.[NH2:28][CH2:29][C@H:30]([OH:39])[CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[OH:39][C@H:30]([CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:29][NH:28][CH:2]1[CH2:3][CH2:4][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)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 1133101(2S)-(-)-1-Amino-3-phenoxy-2-propanolHCID 22220411N-{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide

Product 1

HCID 69654703N-(4-{[4-(4-{[(2S)-2-Hydroxy-3-phenoxypropyl]amino}-1-piperidineyl)anilino]-sulfonyl}phenyl)acetamide

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 (2S)-1-amino-3-phenoxy-propan-2-ol (which was obtained in Example 3) according to the procedure of Example 255 as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.40-1.65 (m, 2H), 1.95-2.10 (m, 2H), 2.06 (s, 3H), 2.50-3.20 (m, 5H), 3.55-3.75 (m, 2H), 3.96 (d, J=5.2 Hz, 2H), 4.15-4.25 (m, 1H), 5.70 (brs, 1H), 6.80 (d, J=9.0 Hz, 2H), 6.88 (d, J=9.0 Hz, 2H), 6.90-7.00 (m, 3H), 7.25-7.35 (m, 2H), 7.59 (d, J=9.0 Hz, 2H), 7.69 (d, J=9.0 Hz, 2H), 9.70 (s, 1H), 10.37 (s, 1H); MS (ES) m/z: 539.1 (MH+); HRMS Calcd. for C28H35N4O5S(MH+): 539.2328. Found: 539.2357.

Sources & evidence

ORD record
ord-27f56c7a27fc4aa287b4a7ec54bef87e
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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