Pyridine → HCID 58424894, compound

HRID 2409440Notes

Reaction equation

HRID 2409440 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:15]3[NH:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:16])[N:8]([CH2:17][O:18][CH3:19])[C:7]=2[CH:20]=1)[CH3:2].[N:21]1[CH:26]=CC=C[CH:22]=1.P(Br)(Br)Br.C(=O)(O)[O-].[Na+].O1CCCC1.CNC>O1CCCC1>[CH3:22][N:21]([CH3:26])[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:15]3[NH:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:16])[N:8]([CH2:17][O:18][CH3:19])[C:7]=2[CH:20]=1)[CH3:2]

Participants

7

Reactant 5

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 22320367Dimethylamine tetrahydrofuranHCID 58424840HCID 58424840, compound

Product 1

HCID 58424894HCID 58424894, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (50 mg, 0.17 mmol) prepared in step 5 was dissolved in tetrahydrofuran (5 ml), sequentially added with pyridine (56 μl, 0.69 mmol) and phosphorus tribromide (33 μl, 0.35 mmol) at room temperature. The resulting mixture was stirred for 3 hours and poured into cold saturated sodium bicarbonate aqueous solution. The mixture was extracted with dichloromethane, washed with brine, dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was then dissolved in tetrahydrofuran (4 ml), and 2.0 M dimethylamine tetrahydrofuran solution (1.7 ml, 3.47 mmol) was added dropwise. The resulting mixture was stirred overnight at room temperature and concentrated to dryness. The residue was purified by flash column chromatography (chloroform:methanol=10:1) to obtain the title compound (15 mg, yield (2 step): 27%, colorless oil).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated to dryness
  5. dissolutionThe residue was then dissolved in tetrahydrofuran (4 ml)
  6. stirringThe resulting mixture was stirred overnight at room temperature
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by flash column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-805fa05a12cb48e9b3c1e67868b3cfd8
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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