Chlorosuccinimide → Tert-butyl 4-{3-[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]-3-oxopropyl}-1-piperidinecarboxylate

HRID 489792Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[O:26])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[CH:4][CH:3]=1.[Cl:27]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)C>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[O:26])[CH2:11][CH2:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:17][CH2:18]2)=[CH:4][C:3]=1[Cl:27]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1,1-dimethylethyl 4-{3-[6-amino-2-(methyloxy)-3-pyridinyl]-3-oxopropyl}-1-piperidinecarboxylate (step 3, 300 mg, 0.825 mmol) and N-chlorosuccinimide (115.7 mg, 0.866mmol) in N,N-dimethylformamide (5 ml) was stirred at 80° C. for 4 h. After cooling to room temperature, the mixture was diluted with diethylether (150 ml), washed with water (50 ml×2) and brine (150 ml), and dried over magnesium sulfate. Removal of solvent gave a brown oil, which was chromatographed on a column of silica gel eluting with ethyl acetate/hexane (2:1) to afford 182 mg (56%) of the title compound as a colorless oil.

Workup

temperatureAfter cooling to room temperature
washwashed with water (50 ml×2) and brine (150 ml)
dry with materialdried over magnesium sulfate
customRemoval of solvent
customgave a brown oil, which
customwas chromatographed on a column of silica gel eluting with ethyl acetate/hexane (2:1)

Sources & evidence

ORD record: ord-aecd30f1d5ae47ad8285d76580cf2f2f
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06979690B2

Reaction notes

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