Tetrahydrofuran → HCID 86704985, compound

HRID 572176Notes

Reaction equation

HRID 572176 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([NH2:22])=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:23]#[C:24]Br.C1COCC1.C(=O)([O-])O.[Na+]>O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:21]3[N:22]=[C:24]2[NH2:23])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 28846536N2-[4-(benzyloxy)phenyl]pyridine-2,3-diamine

Product 1

HCID 86704985HCID 86704985, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N2-[4-(benzyloxy)phenyl]pyridine-2,3-diamine (3.96 g), cyanogen bromide (2.88 g), THF (60 mL) and water (15 mL) was stirred at room temperature for 48 hr. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/tetrahydrofuran), treated with activated carbon, and recrystallized from methanol/water to give the title compound (1.16 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/tetrahydrofuran)
  6. additiontreated with activated carbon
  7. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-d3c9f09c3c9e4741961b2d84b4419bb8
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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