Methyl iodide → N-[2-(3,5-Dicyano-1,2,6-trimethyl-1,4-dihydropyridin-4-yl)furo[3,2-c]pyridin-4-yl]benzamide

HRID 1910671Notes

Reaction equation

HRID 1910671 reaction equation
[C:1]([C:3]1[CH:8]([C:9]2[O:17][C:16]3[CH:15]=[CH:14][N:13]=[C:12]([NH:18][C:19](=[O:26])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:11]=3[CH:10]=2)[C:7]([C:27]#[N:28])=[C:6]([CH3:29])[NH:5][C:4]=1[CH3:30])#[N:2].[C:31](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[C:27]([C:7]1[CH:8]([C:9]2[O:17][C:16]3[CH:15]=[CH:14][N:13]=[C:12]([NH:18][C:19](=[O:26])[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:11]=3[CH:10]=2)[C:3]([C:1]#[N:2])=[C:4]([CH3:30])[N:5]([CH3:31])[C:6]=1[CH3:29])#[N:28]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 10796Cesium carbonateHCID 52938807N-[2-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)furo[3,2-c]pyridin-4-yl]benzamide

Product 1

HCID 52939056N-[2-(3,5-Dicyano-1,2,6-trimethyl-1,4-dihydropyridin-4-yl)furo[3,2-c]pyridin-4-yl]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 100 mg (0.253 mmol) N-[2-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)furo-[3,2-c]pyridin-4-yl]benzamide (Example 4) in DMF (1.4 ml) was cooled to 0° C., and 99 mg (0.30 mmol) caesium carbonate were added at this temperature. After stirring for 30 min, 19 μl (0.30 mmol) methyl iodide were added dropwise at room temperature, and the mixture was stirred at rt overnight. After this, additional methyl iodide (20 μL) was added, and stirring at rt was continued for further 48 h. The reaction mixture was then filtered, and the filtrate was directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA, isocratic 40:60 v/v) to give 5.6 mg (5% of th.) of the title compound.

Workup

  1. stirringthe mixture was stirred at rt overnight
  2. stirringstirring at rt
  3. waitwas continued for further 48 h
  4. filtrationThe reaction mixture was then filtered
  5. customthe filtrate was directly purified by preparative RP-HPLC (acetonitrile/water+0.1% TFA, isocratic 40:60 v/v)

Sources & evidence

ORD record
ord-82ad03ab9687492d90aca41cf543de4e
Source dataset
uspto-grants-2013_12
Patent number
US08604028B2

Reaction notes

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