Pyridine → HCID 86745632, compound

HRID 1029501Notes

Reaction equation

C(N(CC)CC)C.N1C=CC=CC=1.[CH3:14][CH:15]([CH3:20])[CH2:16][C:17](Cl)=[O:18].[Cl:21][C:22]1[N:31]=[C:30]2[C:25]([CH:26]=[CH:27][C:28]([N:32]3[CH:40]([OH:41])[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:33]3=[O:42])=[N:29]2)=[CH:24][CH:23]=1>C(Cl)Cl>[CH3:14][CH:15]([CH3:20])[CH2:16][C:17]([O:41][CH:40]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33](=[O:42])[N:32]1[C:28]1[CH:27]=[CH:26][C:25]2[C:30](=[N:31][C:22]([Cl:21])=[CH:23][CH:24]=2)[N:29]=1)=[O:18]

Participants

Conditions

Temperature: 25 °C

Procedure

Triethylamine (12.2 g), pyridine (90 cc) and then 3-methylbutyryl chloride (9.7 g) is added to a suspension of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-1-isoindolinone (12.5 g) in methylene chloride (600 cc), while the temperature is maintained in the region of 25° C. After 4 hours' stirring at a temperature in the region of 25° C., 3-methylbutyryl chloride (0.7 g) is added again and the mixture is stirred for a further 16 hours at this temperature. The reaction mixture is then concentrated to dryness under reduced pressure (3 kPa) and the residue is taken up with water (500 cc). The insoluble product formed is separated by filtration, washed, dried and then recrystallized in a mixture of isopropyl ether and ethyl acetate (50:50 by volume). 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl 3-methylbutyrate (7.9 g), m.p. 154° C., is thereby obtained.

Workup

additionis added again
concentrationThe reaction mixture is then concentrated to dryness under reduced pressure (3 kPa)
customThe insoluble product formed
customis separated by filtration
washwashed
customdried
customrecrystallized in a mixture of isopropyl ether and ethyl acetate (50:50 by volume)

Sources & evidence

ORD record: ord-b7e8ee875c9b4b29aec71741c5c9e003
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05102890

Reaction notes

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