2-((4-(2-(Cyclopropylmethoxy)ethyl)phenoxy)methyl)oxirane → HCID 70429974, compound

HRID 1906664Notes

Reaction equation

HRID 1906664 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]([CH3:27])[CH2:22][C:23](=[O:26])[NH:24][N:25]=2)=[CH:16][CH:15]=1)=[O:12])C1C=CC=CC=1.[CH:28]1([CH2:31][O:32][CH2:33][CH2:34][C:35]2[CH:45]=[CH:44][C:38]([O:39][CH2:40][CH:41]3[O:43]C3)=[CH:37][CH:36]=2)[CH2:30][CH2:29]1>C(O)CC>[OH:43][CH:41]([CH:40]([CH2:20][C:17]1[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1)[O:39][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][CH2:33][O:32][CH2:31][CH:28]2[CH2:29][CH2:30]2)=[CH:45][CH:44]=1)[CH2:1][NH:8][CH2:9][CH2:10][C:11]([NH:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:21]([CH3:27])[CH2:22][C:23](=[O:26])[NH:24][N:25]=2)=[CH:18][CH:19]=1)=[O:12]

Participants

4

Reactant 2

HCID 117915422-((4-(2-(Cyclopropylmethoxy)ethyl)phenoxy)methyl)oxiraneHCID 14003355HCID 14003355, compound

Product 1

HCID 70429974HCID 70429974, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A mixture of 6-[4-(3-benzylaminopropionamido)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (1.46 g, 0.004 mol), 1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-2,3-epoxypropane (2.0 g, 0.008 mol) (British Pat. No. 1,515,978) and n-propanol was stirred and heated under reflux for 22 hours. Evaporation of the solvent under reduced pressure gave an oily residue which was purified by elution from a silica column with chloroform/methanol mixtures to give 6-[4-[3-[2-hydroxy-3-[4-(2-(cyclopropylmethoxy)ethyl]phenoxy]-N-benzylpropylamino]propionamido]phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone as a foam, 1.3 g, (38%); δ(CHCl3) 0.18 and 0.53 (2m, 4H, cyclopropylmethylene protons), 1.23 (d, 3H, dihydropyridazinone 5-methyl) ppm.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 22 hours
  3. customEvaporation of the solvent under reduced pressure
  4. customgave an oily residue which
  5. customwas purified by elution from a silica column with chloroform/methanol

Sources & evidence

ORD record
ord-5229773deddc45a8969dab74bfe5390d
Source dataset
uspto-grants-1987_03
Patent number
US04652563

Reaction notes

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