Ammonia → 2-(3-(8-Methoxy-1-oxo-1,2-dihydro-2,7-naphthyridin-3-yl)propyl)isoindoline-1,3-dione

HRID 1034940Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][C:15]#[C:16][C:17]1[C:22]([C:23]([O:25]C)=O)=[C:21]([O:27][CH3:28])[N:20]=[CH:19][CH:18]=1.[NH3:29]>CO>[CH3:28][O:27][C:21]1[N:20]=[CH:19][CH:18]=[C:17]2[C:22]=1[C:23](=[O:25])[NH:29][C:15]([CH2:14][CH2:13][CH2:12][N:3]1[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]1=[O:11])=[CH:16]2

Participants

Conditions

Temperature: 115 °C

Procedure

Methyl 4-(5-(1,3-dioxoisoindolin-2-yl)pent-1-ynyl)-2-methoxynicotinate (100 mg, 0.26 mmol) is dissolved in 7% NH3 in MeOH (3 mL) and heated at 115° C. in a sealed tube for 24 hours. The reaction mixture is cooled and the solvents are removed by evaporation. The cyclized product is separated using silica gel column chromatography using hexan:ethyl acetate as solvent. MS m/z 364.1 (M+1).

Workup

temperatureThe reaction mixture is cooled
customthe solvents are removed by evaporation
customThe cyclized product is separated

Sources & evidence

ORD record: ord-4081a06af1a2496bab815e53e4845501
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546370B2

Reaction notes

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