Dimethyl Sulfate → HCID 24770945, compound

HRID 2410077Notes

Reaction equation

HRID 2410077 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([NH:10][C:11]([NH:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=3[CH:25]([CH3:27])[CH3:26])=[O:12])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[Na+].S(OC)(O[CH3:34])(=O)=O>CN(C=O)C.C(OCC)(=O)C>[CH:25]([C:16]1[CH:17]=[C:18]([C:21]([F:23])([F:22])[F:24])[CH:19]=[CH:20][C:15]=1[CH2:14][NH:13][C:11]([NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[N:2][N:1]2[CH3:34])=[O:12])([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 46890599HCID 46890599, compound

Product 1

HCID 24770945HCID 24770945, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 4C (0.468 g, 2.2 mmol) in DMF (6 mL) was added NaH (0.104 g, 2.6 mmol) and the mixture was stirred for 90 minutes. Dimethyl sulfate (Me2SO4, 0.22 mL, 2.3 mmol) was added, and the mixture was stirred for 2 hours. The mixture was diluted with ethyl acetate (1200 mL), washed sequentially with H2O (400 mL) and brine (400 mL), dried (Na2SO4), filtered, concentrated under reduced pressure, and purified by chromatography (75% diethyl ether/Hexanes to 100% diethyl ether) to provide the title compound. 1H-NMR (DMSO-d6) δ 8.81 (s, 1H), 8.04 (s, 1H), 7.64 (d, 1H), 7.60 (s, 1H), 7.55 (m, 2H), 7.25 (t, 1H), 7.14 (d, 1H), 6.81 (t, 1H), 4.49 (d, 2H), 3.99 (s, 3H), 3.30 (m, 1H), 1.25 (d, 6H).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. washwashed sequentially with H2O (400 mL) and brine (400 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified by chromatography (75% diethyl ether/Hexanes to 100% diethyl ether)

Sources & evidence

ORD record
ord-0c9c06b40a3d453583186183b6018f15
Source dataset
uspto-grants-2014_08
Patent number
US08815930B2

Reaction notes

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