1-Bromopropane → HCID 58424956, compound

HRID 2409405Notes

Reaction equation

HRID 2409405 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:22]=[CH:21][C:11]3[NH:12][C:13](=[O:20])[C:14]4[CH:15]=[CH:16][CH:17]=[N:18][C:19]=4[C:10]=3[CH:9]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][CH3:32]>C(#N)C>[CH2:30]([N:1]1[CH2:2][CH2:3][CH:4]([O:7][C:8]2[CH:22]=[CH:21][C:11]3[NH:12][C:13](=[O:20])[C:14]4[CH:15]=[CH:16][CH:17]=[N:18][C:19]=4[C:10]=3[CH:9]=2)[CH2:5][CH2:6]1)[CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 58424971HCID 58424971, compound

Product 1

HCID 58424956HCID 58424956, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Compound (55 mg, 0.17 mmol) prepared in step 4 and potassium carbonate (70 mg, 0.50 mmol) were dissolved in acetonitrile (10 ml), added with 1-bromopropane (53 μl, 0.058 mol) at room temperature. The resulting mixture was stirred overnight at 60° C. and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was then purified by flash column chromatography (chloroform:methanol=5:1) to obtain the title compound (34 mg, yield: 61%, white solid).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was then purified by flash column chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-359e8a8a107d49cf8509f145bc185643
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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