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Ici 109,081 → 6-(4-(3-tert.-Butoxycarbonyl-thiazolidin-2-yl-carbonyl-amino)-phenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone

HRID 1194677
Notes
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Reaction equation

HRID 1194677 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][S:10][CH:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]([CH3:30])[CH2:25][C:26](=[O:29])[NH:27][N:28]=2)=[CH:19][CH:18]=1>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][S:10][CH:9]1[C:13]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:24]([CH3:30])[CH2:25][C:26](=[O:29])[NH:27][N:28]=2)=[CH:19][CH:18]=1)=[O:15])=[O:7])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 161928Ici 109,081HCID 46440943-(tert-Butoxycarbonyl)-1,3-thiazolidine-2-carboxylic acid

Product 1

HCID 137494526-(4-(3-tert.-Butoxycarbonyl-thiazolidin-2-yl-carbonyl-amino)-phenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.5 g (0.032 mole) of 3-tert.-butoxycarbonyl-thiazolidine-2-carboxylic acid and 5.2 g (0.032 mole) of N,N'-carbonyl-diimidazole are heated under reflux in 50 ml of tetrahydrofuran for 15 minutes. After addition of 6.1 g (0.03 mole) of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone, the mixture is stirred at room temperature for 18 hours and concentrated and the residue is crystallised with ethyl acetate.

Workup

  1. concentrationconcentrated
  2. customthe residue is crystallised with ethyl acetate

Sources & evidence

ORD record
ord-037762da13f34779ab8b615cc771aa53
Source dataset
uspto-grants-1989_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04816454

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes