3,3-Dimethylbutanoyl chloride → HCID 11639474, compound

HRID 1817866Notes

Reaction equation

HRID 1817866 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([NH2:20])[C:9]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2].[C:21]([CH2:25][C:26](Cl)=O)([CH3:24])([CH3:23])[CH3:22]>C(OCC)(=O)C>[CH3:22][C:21]([CH3:24])([CH3:23])[CH2:25][C:26]1[N:12]([CH2:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:9]2[CH:10]=[CH:11][C:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])=[CH:7][C:8]=2[N:20]=1

Participants

4

Reactant 2

HCID 815143,3-Dimethylbutanoyl chlorideHCID 68870211HCID 68870211, compound

Product 1

HCID 11639474HCID 11639474, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(ethylsulfonyl)-N′-(tetrahydro-2H-pyran-4-ylmethyl)benzene-1,2-diamine (Step B) in ethyl acetate (16 mL) was added tert-butylacetyl chloride (0.1 mL, 0.8 mmol) at room temperature. After stirring for 2 h, the mixture was quenched with water and extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The residue was dissolved in ethanol and 2N sodium hydroxide solution. The mixture was microwaved for 30 min at 130° C. The reaction mixture was quenched with water and extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by amine coated silica gel column chromatography (hexane:ethyl acetate=2:1 as eluent) to afford the title compound (103 mg, 34%) as a white solid.

Workup

  1. customthe mixture was quenched with water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in ethanol
  7. customThe mixture was microwaved for 30 min at 130° C
  8. customThe reaction mixture was quenched with water
  9. extractionextracted three times with ethyl acetate
  10. dry with materialThe combined organic layers were dried over magnesium sulfate
  11. filtrationfiltered
  12. customThe filtrate was evaporated under reduced pressure
  13. customThe residue was purified by amine coated silica gel column chromatography (hexane:ethyl acetate=2:1 as eluent)

Sources & evidence

ORD record
ord-682f1a67673148419357730e156895b4
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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