Potassium Carbonate → HCID 86683879, compound

HRID 1620109Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([F:10])=[C:4](Cl)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:18][C@H:19]([CH3:32])[CH2:20][N:21]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:31].Cl.C(=O)([O-])O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:18][C@H:19]([CH3:32])[CH2:20][N:21]2[C:22](=[O:31])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]2=[O:30])[C:5]([F:10])=[CH:6][C:7]=1[C:8]#[N:9]

Participants

Conditions

Temperature: 60 °C

Procedure

2,6-dichloro-5-fluoro-3-pyridinecarbonitrile (3.3 g) and potassium carbonate (1.1 g) were added to a DMF (5 ml) solution containing (R)-2-(2-aminopropyl)isoindoline-1,3-dione•hydrochloride (690 mg), followed by stirring with heating at 60° C. for 5.5 hours. The reaction solution was adjusted to room temperature, and a saturated aqueous sodium hydrogen carbonate solution was added, followed by extraction with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the residue was purified by silica gel chromatography (n-hexane:ethyl acetate=7:3, and a yellow solid of (R)-2-chloro-6-((1-(1,3-dioxoisoindolin-2-yl)propan-2-yl)amino)-5-fluoronicotinonitrile (300 mg) was thus obtained.

Workup

customwas adjusted to room temperature
extractionfollowed by extraction with ethyl acetate
dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
distillationSubsequently, the solvent was distilled away under reduced pressure
customthe residue was purified by silica gel chromatography (n-hexane

Sources & evidence

ORD record: ord-73a2880f617e4d2793f1b58751b71a5f
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772320B2

Reaction notes

Loading…