Dimethyl Sulfate → HCID 24770945, compound

HRID 499941Notes

Reaction equation

HRID 499941 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-fbd28f498d8d42c1a3afea96e4785a9a
Source dataset
uspto-grants-2010_08
Patent number
US07767705B2

Reaction notes

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