Iodoethane → HCID 86630218, compound

HRID 548599Notes

Reaction equation

HRID 548599 reaction equation
[Cl:1][C:2]1[C:11]2=[N:12][N:13]([CH2:23][CH2:24][CH3:25])[C:14]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[CH2:26](I)[CH3:27].[H-].[Na+].[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[C:11]2=[N:12][N:13]([CH2:23][CH2:24][CH3:25])[C:14]([N:15]([CH2:26][CH3:27])[C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 6340Iodoethane2×HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86630219HCID 86630219, compound

Product 1

HCID 86630218HCID 86630218, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-chloro-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-ylcarbamate (722 mg, 2.00 mmol) in THF (5 mL) was added ethyl iodide (624 mg, 4.0 mmol). Sodium hydride (120 mg of a 60 wt % dispersion in mineral oil, 3.00 mmol) was added, and after 40 min, more ethyl iodide (624 mg, 2.00 mmol) was added, and the reaction was stirred overnight. Saturated ammonium chloride was added, and the aqueous layer was extracted with methyl tert-butyl ether (3×). The combined organic layers were dried (magnesium sulfate), filtered, concentrated, and purified by prep HPLC (silica cartridge, eluting with ethyl acetate in hexane) to afford 718 mg of tert-butyl 4-chloro-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl(ethyl)carbamate as a white solid.

Workup

  1. extractionthe aqueous layer was extracted with methyl tert-butyl ether (3×)
  2. dry with materialThe combined organic layers were dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by prep HPLC (silica cartridge, eluting with ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1e0a72fbd63f4a60bf9dd6c532757507
Source dataset
uspto-grants-2011_05
Patent number
US07943610B2

Reaction notes

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