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1-(Carboxymethyl)cyclopentanecarboxylic acid → 2-[3-(4-Oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-azaspiro[4.4]nonane-1,3-dione

HRID 459752
Notes
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Reaction equation

HRID 459752 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[NH:8][N:7]=1.[C:20]([CH2:23][C:24]1([C:29](O)=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]1)(O)=[O:21]>CO>[O:16]=[C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([CH2:5][C:4]2[CH:3]=[C:2]([N:1]3[C:20](=[O:21])[CH2:23][C:24]4([CH2:28][CH2:27][CH2:26][CH2:25]4)[C:29]3=[O:30])[CH:19]=[CH:18][CH:17]=2)=[N:7][NH:8]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2582911-(Carboxymethyl)cyclopentanecarboxylic acidHCID 184443754-(3-aminobenzyl)-2H-phthalazin-1-one

Product 1

HCID 184443482-[3-(4-Oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-azaspiro[4.4]nonane-1,3-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
200 °C

Procedure

A stirred mixture of 4-(3-aminobenzyl)-2H-phthalazin-1-one (0.1 g, 0.4 mmol; prepared in a manner similar to that described in Example 1) and 1-(carboxymethyl)cyclopentanecarboxylic acid (0.0685 g, 0.4 mmol) was heated at 200° C. for 2.5 hours then it was allowed to cool to ambient temperature. Methanol (1 ml) was added and the mixture was heated under reflux for 5 minutes. No solid precipitated, so the mixture was concentrated in vacuo and the residue was triturated with water (5 ml). The resulting solid was collected by filtration and dried in vacuo to give 2-[3-(4-oxo-3,4-dihydrophthalazin-1-ylmethyl)phenyl]-2-azaspiro[4.4]nonane-1,3-dione (0.108 g) as a brown solid, m/z (M+H)+. 388, 89.1% purity.

Workup

  1. customprepared in a manner similar to
  2. temperatureto cool to ambient temperature
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 5 minutes
  5. customNo solid precipitated, so the mixture
  6. concentrationwas concentrated in vacuo
  7. customthe residue was triturated with water (5 ml)
  8. filtrationThe resulting solid was collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-5b3a6afd2f5743e8bbd3966c2726f322
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07196085B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes