Water → HCID 57225320, compound

HRID 1029492Notes

Reaction equation

[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([O-:13])=[O:12])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Na+].Cl[CH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=[O:25])[N:17]1[C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[N:29][C:30]([Cl:36])=[CH:31][CH:32]=2)[N:27]=1.N12CCCN=C1CCCCC2.O>CN(C)C=O>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([O:13][CH:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18](=[O:25])[N:17]2[C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[N:29][C:30]([Cl:36])=[CH:31][CH:32]=3)[N:27]=2)=[O:12])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

Sodium (4-acetyl-1-piperazinyl)acetate (4.2 g) is added to a solution, maintained at a temperature in the region of 20° C., of 3-chloro-2-(7-chloro-1,8-naphthyridin-2yl)-1-isoindolinone (6.6 g) in anhydrous dimethylformamide (60 cc), and the reaction mixture is maintained for 15 hours at a temperature in the region of 20° C. 1,8-Diazabicyclo[5.4.0]undec-7-ene (3g) is then added, and the mixture is then stirred again for 24 hours at a temperature in the region of 20° C. The reaction mixture is taken up with water (250 cc) and extracted with methylene chloride (3×150 cc). After the organic phase has been washed with water and concentrated to dryness under reduced pressure (2.7 kPa), the residue obtained is recrystallized in ethanol. 2-(7-Chloro-1,8-naphthyridin-2-yl-)-3-oxo-1-isoindolinyl (4-acetyl-1-piperazinyl)acetate (3.7 g), m.p. 192° C., is thereby obtained.

Workup

extractionextracted with methylene chloride (3×150 cc)
washAfter the organic phase has been washed with water
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
customthe residue obtained
customis recrystallized in ethanol

Sources & evidence

ORD record: ord-a5cbc93c00814c67be3cac2ce13ac419
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05102890

Reaction notes

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