Water → HCID 56592175, compound

HRID 2404246Notes

Reaction equation

HRID 2404246 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:27][CH3:28])=[CH:5][C:6]2[C:7]3[C:15]([C:16]4[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([CH2:24][OH:25])[CH:17]=4)=[N:14][N:13]([CH3:26])[C:8]=3[CH:9]=[N:10][C:11]=2[CH:12]=1.[CH3:29]I.[H-].[Na+].O>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([O:27][CH3:28])=[CH:5][C:6]2[C:7]3[C:15]([C:16]4[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([CH2:24][O:25][CH3:29])[CH:17]=4)=[N:14][N:13]([CH3:26])[C:8]=3[CH:9]=[N:10][C:11]=2[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66632686HCID 66632686, compound

Product 1

HCID 56592175HCID 56592175, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-(7,8-Dimethoxy-3-methyl-3H-pyrazolo[3,4-c]quinolin-1-yl)-2-hydroxymethylbenzonitrile (17 mg, 44 μmol) is dissolved in N,N-dimethylformamide (2.1 ml) under argon, and methyl iodide (8.2 μl, 131 μmol) and sodium hydride (95%, 2.4 mg, 96 μmol) are subsequently added. The reaction solution is stirred at 0° C. for 2 h. After addition of a little water, the mixture is extracted with ethyl acetate and semi-saturated sodium chloride solution for work-up. The organic phase is dried over Na2SO4, filtered with suction and evaporated to dryness at 40° C. in vacuo. The residue is purified by chromatography (pHPLC, solvent gradient water/1-30% by vol. of acetonitrile, 0.1% by vol. of formic acid), and the product fractions are freeze-dried, giving 4-(7,8-dimethoxy-3-methyl-3H-pyrazolo[3,4-c]quinolin-1-yl)-2-methoxymethylbenzonitrile (4 mg, 10.3 μmol) as a colourless solid. MS: 389.2 (M+H+), TLC (HPTLC): Rf=0.41 (ethyl acetate/ethanol 8:1, parts by volume).

Workup

  1. extractionthe mixture is extracted with ethyl acetate and semi-saturated sodium chloride solution for work-up
  2. dry with materialThe organic phase is dried over Na2SO4
  3. filtrationfiltered with suction
  4. customevaporated to dryness at 40° C. in vacuo
  5. customThe residue is purified by chromatography (pHPLC, solvent gradient water/1-30% by vol. of acetonitrile, 0.1% by vol. of formic acid)
  6. customthe product fractions are freeze-dried

Sources & evidence

ORD record
ord-98ad99def0dc46a1ac13754a4c1fef1e
Source dataset
uspto-grants-2014_08
Patent number
US08802712B2

Reaction notes

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