1-(3-Aminophenyl)ethanol → HCID 66762110, compound

HRID 1397935Notes

Reaction equation

HRID 1397935 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:22])[S:10]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:5][CH:4]=1.[NH2:23][C:24]1[CH:25]=[C:26]([CH:30]([OH:32])[CH3:31])[CH:27]=[CH:28][CH:29]=1>>[OH:32][CH:30]([C:26]1[CH:25]=[C:24]([NH:23][C:17](=[O:19])[C:16]2[CH:15]=[CH:14][C:13]([S:10](=[O:12])(=[O:11])[N:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH3:22])=[CH:21][CH:20]=2)[CH:29]=[CH:28][CH:27]=1)[CH3:31]

Participants

3

Reactant 2

HCID 2224611-(3-Aminophenyl)ethanolHCID 66762693HCID 66762693, compound

Product 1

HCID 66762110HCID 66762110, compound

Procedure

4-(N-(4-methoxyphenyl)-N-methylsulfamoyl)benzoic acid (7) (100 mg, 0.31 mmol) was treated with 1-(3-aminophenyl)ethanol (36 mg, 0.26 mmol) using method C. The residue was purified using flash chromatography eluting with 0-40% EtOAc in hexanes. The resulting solid was triturated with dichloromethane/hexanes to give N-(3-(1-hydroxyethyl)phenyl)-4-(N-(4-methoxyphenyl)-N-methylsulfamoyl)benzamide as an off white solid. Yield: 52 mg (46%). 1H-NMR: 10.45 (s, 1H), 8.12 (d, J=8.5 Hz, 2H), 7.75-7.74 (m, 1H), 7.68-7.64 (m, 3H), 7.30 (t, J=8.0 Hz, 1H), 7.10 (d, J=8.0 Hz, 1H), 7.01 (d, J=8.0 Hz, 2H), 6.90 (d, J=8.0 Hz, 2H), 5.19 (d, J=4.5 Hz, 1H), 4.75-4.68 (m, 1H), 3.75 (s, 3H), 3.15 (s, 3H), 1.33 (d, J=6.5 Hz, 3H).

Workup

  1. customThe residue was purified
  2. washeluting with 0-40% EtOAc in hexanes
  3. customThe resulting solid was triturated with dichloromethane/hexanes

Sources & evidence

ORD record
ord-e11305212d294a81b66911c471b33bdf
Source dataset
uspto-grants-2014_12
Patent number
US08901306B2

Reaction notes

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