4-(2-Amino-1-hydroxyethyl)benzene-1,3-diol → N-(4-{[4-(4-{[2-(2,4-Dihydroxyphenyl)-2-hydroxyethyl]amino}-1-piperidineyl)-anilino]sulfonyl}phenyl)acetamide

HRID 1794874Notes

Reaction equation

HRID 1794874 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][CH:30]([C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][C:33]=1[OH:39])[OH:31]>>[OH:39][C:33]1[CH:34]=[C:35]([OH:38])[CH:36]=[CH:37][C:32]=1[CH:30]([OH:31])[CH2:29][NH:28][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:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=3)(=[O:16])=[O:17])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 167683114-(2-Amino-1-hydroxyethyl)benzene-1,3-diolHCID 22220411N-{4-[4-(4-Oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide

Product 1

HCID 22220536N-(4-{[4-(4-{[2-(2,4-Dihydroxyphenyl)-2-hydroxyethyl]amino}-1-piperidineyl)-anilino]sulfonyl}phenyl)acetamide

Procedure

The title compound was prepared from N-{4-[4-(4-oxo-piperidin-1-yl)-phenylsulfamoyl]-phenyl}-acetamide (which was obtained in Example 216) and 2-amino-1-(2,4-dihydroxy-phenyl)-ethanol according to the procedure of Example 255 as a pale yellowish solid; 1H NMR (300 MHz, DMSO-d6) δ 1.55–1.75 (m, 2 H), 1.95–2.15 (m, 2 H), 2.08 (s, 3 H), 2.50–3.20 (m, 5 H), 3.60–3.70 (m, 2 H), 5.04–5.10 (m, 1 H), 6.65–6.75 (m, 1 H), 6.24 (dd, J=8.1, 2.1 Hz, 1 H), 6.32 (d, J=2.1 Hz, 1 H), 6.80 (d, J=9.0 Hz, 2 H), 6.88 (d, J=9.0 Hz, 2 H), 7.12 (d, J=8.1 Hz, 1 H), 7.59 (d, J=9.0 Hz, 2 H), 7.70 (d, J=9.0 Hz, 2 H), 9.26 (s, 1 H), 9.71 (brs, 1 H), 10.44 (s, 1 H); MS (ES) m/z: 541.4 (MH+); HRMS Calcd. for C27H33N4O6S (MH+): 541.2121. Found: 541.2084.

Sources & evidence

ORD record
ord-4db446e65d6f43f5a14d27a64fdb1d88
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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