Methanol → 1-[2-(3-Carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[3-(1,5-dimethylpyrrol-2-yl)-phenoxy]-2-propanol

HRID 638065Notes

Reaction equation

HRID 638065 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][CH:4]=[C:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH:16]2[O:18][CH2:17]2)[CH:9]=1.[NH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:31]=[C:27]([C:28]([NH2:30])=[O:29])[C:26]([OH:32])=[CH:25][CH:24]=1.CO>C(O)(C)C>[C:28]([C:27]1[CH:31]=[C:23]([CH:24]=[CH:25][C:26]=1[OH:32])[O:22][CH2:21][CH2:20][NH:19][CH2:17][CH:16]([OH:18])[CH2:15][O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([C:3]2[N:2]([CH3:1])[C:6]([CH3:7])=[CH:5][CH:4]=2)[CH:9]=1)(=[O:29])[NH2:30]

Participants

5

Reactant 3

HCID 887MethanolHCID 202551361,5-Dimethyl-2-[3-(2,3-epoxypropoxy)-phenyl]-pyrroleHCID 230496945-(2-Aminoethoxy)-2-hydroxybenzamide

Product 1

HCID 202551411-[2-(3-Carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[3-(1,5-dimethylpyrrol-2-yl)-phenoxy]-2-propanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Solutions of 5.0 g of crude 1,5-dimethyl-2-[3-(2,3-epoxypropoxy)-phenyl]-pyrrole in 15 ml of isopropanol and of 3.0 g of 5-(2-aminoethoxy)-salicylamide in 30 ml of isopropanol are combined and boiled under reflux for 2.5 hours. A portion of the precipitated reaction product is dissolved by the addition of 50 ml of methanol. The filtered solution is evaporated to dryness and the residue is recrystallised twice from ethyl acetate, yielding 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[3-(1,5-dimethylpyrrol-2-yl)-phenoxy]-2-propanol having a melting point of 108°-112°.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. customA portion of the precipitated reaction product
  3. customThe filtered solution is evaporated to dryness
  4. customthe residue is recrystallised twice from ethyl acetate

Sources & evidence

ORD record
ord-4c5e2b91807f4d00a1bedfc1d7f8310b
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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