alpha-(3,4-Dimethoxyphenyl)benzeneethanamine → N-[3-[2-[[1-(3,4-Dimethoxyphenyl)-2-phenylethyl]amino]1-hydroxyethyl]phenyl]methanesulfonamide

HRID 1955794Notes

Reaction equation

HRID 1955794 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH2:19])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH:25]=1)=[O:23]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH:19][CH2:21][CH:22]([C:24]2[CH:25]=[C:26]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[CH:27]=[CH:28][CH:29]=2)[OH:23])[CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

3

Reactant 2

HCID 411116alpha-(3,4-Dimethoxyphenyl)benzeneethanamineHCID 11346858N-[3-(2-bromoacetyl)phenyl]methanesulfonamide

Product 1

HCID 19073125N-[3-[2-[[1-(3,4-Dimethoxyphenyl)-2-phenylethyl]amino]1-hydroxyethyl]phenyl]methanesulfonamide

Procedure

The title compound was prepared by coupling α-(3,4-dimethoxyphenyl)benzeneethanamine, prepared as described in step C of Example 1, with 2-bromo-1-[3-[(methylsulfonyl)amino]phenyl]ethanone via the procedure described in step D of Example 1. The title compound, after silica gel chromatography, was purified by preparative HPLC using 49% solvent B to elute the desired material from a YMC S10 C18 column.

Workup

  1. customprepared
  2. customThe title compound, after silica gel chromatography, was purified by preparative HPLC
  3. washto elute the desired material from a YMC S10 C18 column

Sources & evidence

ORD record
ord-a83721cb05a348c7adf3f8e5a081c474
Source dataset
uspto-grants-1998_07
Patent number
US05776983

Reaction notes

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