Water → HCID 11325986, compound

HRID 1246970Notes

Reaction equation

HRID 1246970 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:22]=[CH:21][C:17]3[O:18][CH2:19][O:20][C:16]=3[CH:15]=2)[C:9]([C:23]#[N:24])=[C:8]([NH2:25])[N:7]=1)[CH3:2].[H-].[Na+].[CH3:29]I.O>CN(C=O)C>[NH2:25][C:8]1[N:7]=[C:6]([CH:5]([CH3:29])[C:4]([O:3][CH2:1][CH3:2])=[O:26])[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:22]=[CH:21][C:17]3[O:18][CH2:19][O:20][C:16]=3[CH:15]=2)[C:9]=1[C:23]#[N:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 9928346HCID 9928346, compound

Product 1

HCID 11325986HCID 11325986, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl[6-amino-4-(1,3-benzodioxol-5-yl)-3,5-dicyano-2-pyridinyl]acetate (step 1) (2.00 g, 5.71 mmol) is initially charged in 40 ml of DMF. Sodium hydride (0.37 g, 9.19 mmol) is added and the mixture is stirred for 45 minutes. Methyl iodide (0.40 ml, 6.39 mmol) is then added, the color of the yellow reaction solution turning to orange. After five hours, a further 0.2 ml of methyl iodide is added and the mixture is stirred at room temperature overnight. The mixture is poured into water (50 ml), and an emulsion is formed. The emulsion is extracted three times with ether. The combined organic phases are dried over magnesium sulfate, filtered and concentrated using a rotary evaporator. The mixture is chromatographed by RP-HPLC using an acetonitrile/water gradient. The product is obtained as a colorless solid.

Workup

  1. waitAfter five hours
  2. stirringthe mixture is stirred at room temperature overnight
  3. customan emulsion is formed
  4. extractionThe emulsion is extracted three times with ether
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customa rotary evaporator
  9. customThe mixture is chromatographed by RP-HPLC
  10. customThe product is obtained as a colorless solid

Sources & evidence

ORD record
ord-625d9c5eb4e94b72bf95def862c25704
Source dataset
uspto-grants-2006_10
Patent number
US07129255B2

Reaction notes

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