Nicotinic Acid → HCID 10311350, compound

HRID 491788Notes

Reaction equation

HRID 491788 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH:9][C:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][C:11]=2[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=2)=[O:20])=[O:8])[CH2:3][CH2:2]1.[C:29](O)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>CN(C)C=O.O>[N:32]1[CH:33]=[CH:34][CH:35]=[C:30]([C:29]([N:1]2[CH2:6][CH2:5][CH:4]([C:7]([NH:9][C:10]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[O:12][C:11]=3[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=3)=[O:20])=[O:8])[CH2:3][CH2:2]2)=[O:36])[CH:31]=1

Participants

8

Reactant 5

HCID 938Nicotinic AcidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23062699HCID 23062699, compound

Product 1

HCID 10311350HCID 10311350, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-[(Piperidin-4-yl)carbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (100 mg) obtained in Example 228 is dissolved in N,N-dimethylformamide (3 ml), and thereto are added successively nicotinic acid (34 mg), 1-hydroxybenzotriazole (37 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (53 mg), and the mixture is stirred at room temperature for 4 hours. To the reaction solution are poured a saturated aqueous sodium hydrogen carbonate solution and water, and the precipitates are collected by filtration, washed with chloroform, and dried to give 3-[1-((pyridin-3-yl)carbonyl)piperidin-4-ylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (103 mg). This product is treated with hydrogen chloride in dioxane to give the title compound (115 mg).

Workup

  1. filtrationthe precipitates are collected by filtration
  2. washwashed with chloroform
  3. customdried

Sources & evidence

ORD record
ord-dbe2ef11cd8c4b988fa435d320b19b7d
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

Loading…