Potassium Carbonate → 6-Amino-N-[(1-Butyl-4-Piperidinyl)Methyl]-2-Oxo-1,2-Dihydro-3-Pyridinecarboxamide

HRID 489807Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([O:8]C)[C:5]([C:10]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:15]2)=[O:11])=[CH:4][C:3]=1I.CC1NC=CN=1.C(=O)([O-])[O-].[K+].[K+]>[Cu]>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:10]([NH:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19]2)=[O:11])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 6-amino-N-[(1-butyl-4-piperidinyl)methyl]-5-iodo-2-(methyloxy)-3-pyridinecarboxamide (step 3, 112 mg, 0.25 mmol), 2-methylimidazole (420 mg, 5 mmol), copper powder (32 mg, 0.5 mmol) and potassium carbonate (69 mg, 0.5 mmol) was heated at 140° C. for 25 min, 150° C. for 30 min and 160° C. for 45 min. After cooling, the mixture was chromatographed on a column of silica gel eluting with 25% ammonium hydroxide/methanol/dichloromethane (1:10:90) to give 35 mg (46%) of the title compound as a pale yellow solid.

Workup

temperatureAfter cooling
customthe mixture was chromatographed on a column of silica gel eluting with 25% ammonium hydroxide/methanol/dichloromethane (1:10:90)

Sources & evidence

ORD record: ord-f59eff57388b42048b070cd55c81b47a
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06979690B2

Reaction notes

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