5-[2-(Benzylamino)-ethoxy]-salicylamide → 1-[N-benzyl-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]]-3-[2-(indol-2-yl)-phenoxy]-2-propanol

HRID 638040Notes

Reaction equation

HRID 638040 reaction equation
[O:1]1[CH2:20][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.[CH2:21]([NH:28][CH2:29][CH2:30][O:31][C:32]1[CH:40]=[C:36]([C:37]([NH2:39])=[O:38])[C:35]([OH:41])=[CH:34][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)(C)C>[CH2:21]([N:28]([CH2:29][CH2:30][O:31][C:32]1[CH:33]=[CH:34][C:35]([OH:41])=[C:36]([C:37](=[O:38])[NH2:39])[CH:40]=1)[CH2:20][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 137544195-[2-(Benzylamino)-ethoxy]-salicylamideHCID 202551792-[2-(2,3-Epoxypropoxy)-phenyl]-indole

Product 1

HCID 202550651-[N-benzyl-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]]-3-[2-(indol-2-yl)-phenoxy]-2-propanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The starting compound is obtained in the following manner: (13a) A solution of 10.5 g of 2-[2-(2,3-epoxypropoxy)-phenyl]-indole and 10.2 g of 5-(2-benzylaminoethoxy)-salicylamide in 300 ml of isopropanol is reacted analogously to Example 4(c) and yields crude 1-[N-benzyl-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]]-3-[2-(indol-2-yl)-phenoxy]-2-propanol in the form of an orange resin that is further processed in that form.

Workup

  1. customThe starting compound is obtained in the following manner

Sources & evidence

ORD record
ord-71ff6cf360a54cf4b9d23b210e614742
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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