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Isopropylamine → 2,6-Dihydro-2-methyl-6-(1-naphthalenylmethyl)-4-(2-propyl)amino-1H-pyrrolo[3,4-d]pyridazin-1-one

HRID 1835153
Notes
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Reaction equation

HRID 1835153 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].Cl[C:6]1[C:7]2[C:8](=[CH:14][N:15]([CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)[CH:16]=2)[C:9](=[O:13])[N:10]([CH3:12])[N:11]=1>C(O)C>[CH3:12][N:10]1[C:9](=[O:13])[C:8]2=[CH:14][N:15]([CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)[CH:16]=[C:7]2[C:6]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:11]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 235032554-Chloro-2,6-dihydro-2-methyl-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyridazin-1-one

Product 1

HCID 235032472,6-Dihydro-2-methyl-6-(1-naphthalenylmethyl)-4-(2-propyl)amino-1H-pyrrolo[3,4-d]pyridazin-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

Isopropylamine (1 ml) was added to a solution of 4-chloro-2,6-dihydro-2-methyl-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyridazine-1-one (0.095 g) in ethanol (4 ml) and the mixture was heated in a sealed tube at 200° C. for 3 days then at 250° C. for 24 hours. The mixture was evaporated and the residue was purified by column chromatography, eluting with ethyl acetate followed by recrystallisation from ethyl acetate/isohexane to give the title compound (0.013 g).

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography
  3. washeluting with ethyl acetate
  4. customfollowed by recrystallisation from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-e4484745bf3d4f51b5bcc7c5a4fabdbc
Source dataset
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06770646B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes