Dimethylformamide → HCID 57647294, compound

HRID 400563Notes

Reaction equation

HRID 400563 reaction equation
[CH3:1][CH:2]([CH3:31])[CH2:3][C:4]([NH:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2C=C[N:15]=[C:14]3[N:18]([S:21]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH:19]=[CH:20][C:13]=23)[N:11]=1)=[O:5].[H-].[Na+].[CH2:34](I)[CH2:35][CH3:36].[CH3:38][N:39](C=O)C>>[CH3:1][CH:2]([CH3:31])[CH2:3][C:4]([N:6]([CH2:34][CH2:35][CH3:36])[C:7]1[S:8][CH:9]=[C:10]([C:12]2[C:13]3[CH:20]=[CH:19][N:18]([S:21]([C:24]4[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=4)(=[O:23])=[O:22])[C:14]=3[N:15]=[CH:38][N:39]=2)[N:11]=1)=[O:5]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 86629117HCID 86629117, compound

Product 1

HCID 57647294HCID 57647294, compoundYield 76%

Conditions

Temperature
40 °C

Procedure

[100 mg; 0.22 mmol] of 3-Methyl-N-{4-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-thiazol-2-yl}-butyramide was dissolved in 1 mL of dry DMF and to this solution was added [13.0 mg; 0.27 mmol] of sodium hydride (60% in oil dispersion) and the reaction was stirred at 40° C. for 10 minutes before addition of [21.5 uL; 37.37 mg; 0.22 mmol] of n-propyliodide, in one portion. The reaction was stirred for one hour more at 40° C. After reaction was determined to be complete, the solvent was removed under reduced pressure and residue triturated with methyl t-butyl ether and filtrate decanted away from oil. The trituration was performed again and the crude reaction mixture stirred overnight at ambient temperature, the material solidifies. The material was isolated via suction filtration and washed with more ether, again with petroleum ether and air dried. This provides a dark beige powder; 83 mg representing a 76% yield.

Workup

  1. customAfter reaction
  2. customthe solvent was removed under reduced pressure and residue
  3. customtriturated with methyl t-butyl ether and filtrate
  4. customdecanted away from oil
  5. customthe crude reaction mixture
  6. stirringstirred overnight at ambient temperature
  7. customThe material was isolated via suction filtration
  8. washwashed with more ether, again with petroleum ether and air
  9. customdried
  10. customThis provides a dark beige powder

Sources & evidence

ORD record
ord-c8653cefded946b497b027fb04ce5664
Source dataset
uspto-grants-2014_06
Patent number
US08741912B2

Reaction notes

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