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HCID 70429974, compound → 6-(4-(3-((2-hydroxy-3-(4-(2-(cyclopropylmethoxy)ethyl)phenoxy)propyl)amino)propionamido)phenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone

HRID 1906671
Notes
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Reaction equation

HRID 1906671 reaction equation
[OH:1][CH:2]([CH:24](CC1C=CC=CC=1)[O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][O:34][CH2:35][CH:36]2[CH2:38][CH2:37]2)=[CH:28][CH:27]=1)[CH2:3][NH:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]([CH3:23])[CH2:18][C:19](=[O:22])[NH:20][N:21]=2)=[CH:12][CH:11]=1)=[O:8].[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[OH:1][CH:2]([CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][O:34][CH2:35][CH:36]2[CH2:38][CH2:37]2)=[CH:28][CH:27]=1)[CH2:3][NH:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:17]([CH3:23])[CH2:18][C:19](=[O:22])[NH:20][N:21]=2)=[CH:14][CH:15]=1)=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 70429974HCID 70429974, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 1833506-(4-(3-((2-hydroxy-3-(4-(2-(cyclopropylmethoxy)ethyl)phenoxy)propyl)amino)propionamido)phenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinoneYield 79.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst
HCID 702
Ethanol
Solvent

Procedure

In a manner similar to that of Example 1 (iv), 6-[4-[3-[2-hydroxy-3-[4-(2-(cyclopropylmethoxy)ethyl)phenoxy]-N-benzylpropylamino]propionamido]phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (22 g) in ethanol (350 ml) was agitated for 5 hours in a hydrogen atmosphere at 344 kPa (50 p.s.i.) in the presence of palladium hydroxide on charcoal (5 g). The catalyst was removed by filtration and solvent removed under reduced pressure to afford the title compound as a yellow foam (15 g). To a solution of this in dichloromethane (800 ml) was added a solution of methanesulphonic acid (8.60 g) in dichloromethane (100 ml) with stirring. The mixture was evaporated under reduced pressure to give a yellow solid which was crystallised from isopropanol/ethanol (50:50; 400 ml) to yield the title compound as the monomethanesulphonate salt (16 g), m.p. 185°-6° C. Conversion of this material (from another run) by base formation and retreatment with methanesulphonic acid afforded material with m.p. 186°-7° C.

Workup

  1. customThe catalyst was removed by filtration and solvent
  2. customremoved under reduced pressure

Sources & evidence

ORD record
ord-3dbca490444b40dfb784fc8e98f93cc9
Source dataset
uspto-grants-1987_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04652563

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes