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

HRID 459752Notes

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

Participants

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

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