Iodoethane → 6-Amino-5-chloro-N-[(1-ethyl-4-piperidinyl)methyl]-2-oxo-1,2-dihydro-3-pyridinecarboxamide

HRID 489784Notes

Reaction equation

Cl.Cl.[NH2:3][C:4]1[NH:9][C:8](=[O:10])[C:7]([C:11]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[O:12])=[CH:6][C:5]=1[Cl:21].I[CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:3][C:4]1[NH:9][C:8](=[O:10])[C:7]([C:11]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([CH2:23][CH3:24])[CH2:17][CH2:16]2)=[O:12])=[CH:6][C:5]=1[Cl:21]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 6-amino-5-chloro-2-oxo-N-(4-piperidinylmethyl)-1,2-dihydro-3-pyridinecarboxamide dihydrochloride (step 2, 100 mg, 0.28 mmol), iodoethane (49 mg, 0.31 mmol) and potassium carbonate (172 mg, 1.25 mmol) in N,N-dimethylformamide (6 ml) was stirred at 60° C. for 15 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was suspended in tetrahydrofuran (50 ml), and the solution was filtered through a pad of Celite. The filtrate was concentrated in vacuo, and the obtained residue was chromatographed on a column of aminopropyl silica gel eluting with methanol/dichloromethane (1:2.5) to give 43 mg (49%) of the title compound as a white solid.

Workup

temperatureAfter cooling to room temperature
customthe solvent was removed in vacuo
filtrationthe solution was filtered through a pad of Celite
concentrationThe filtrate was concentrated in vacuo
customthe obtained residue was chromatographed on a column of aminopropyl silica gel eluting with methanol/dichloromethane (1:2.5)

Sources & evidence

ORD record: ord-1a2e730f145440e69cc9ac4b321c54cc
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06979690B2

Reaction notes

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