Butyl bromide → HCID 66851701, compound

HRID 538822Notes

Reaction equation

HRID 538822 reaction equation
[S:1]1[C:5]2[CH2:6][CH2:7][O:8][CH2:9][C:4]=2[N:3]=[C:2]1[NH2:10].Br[CH2:12][CH2:13][CH2:14][CH3:15]>CN(C=O)C>[CH2:12]([N:3]1[C:4]2[CH2:9][O:8][CH2:7][CH2:6][C:5]=2[S:1][C:2]1=[NH:10])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 8002Butyl bromideHCID 86624873HCID 86624873, compound

Product 1

HCID 66851701HCID 66851701, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 96A (290 mg, 1.86 mmol) and 1-bromobutane (220 μL, 2.0 mmol) in DMF (400 μL) was heated at 95° C. for 16 hr, cooled to room temperature and quenched with 5 mL of aqueous 1M NaHCO3 solution. The aqueous layer was extracted with dichloromethane (3×5 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated to afford 0.4 g of the crude product of the title compound. LC/MS (ESI+) m/z 213 (M+H)+.

Workup

  1. customquenched with 5 mL of aqueous 1M NaHCO3 solution
  2. extractionThe aqueous layer was extracted with dichloromethane (3×5 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7a8dfc40503c4c97b056ad6c429125fb
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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