Tetrahydrofuran → HCID 86704992, compound

HRID 572188Notes

Reaction equation

HRID 572188 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([NH2:22])=[C:20]([CH3:23])[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:24]#[C:25]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][C:20]([CH3:23])=[C:21]3[N:22]=[C:25]2[NH2:24])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 58577506N2-[4-(benzyloxy)phenyl]-4-methylpyridine-2,3-diamine

Product 1

HCID 86704992HCID 86704992, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N2-[4-(benzyloxy)phenyl]-4-methylpyridine-2,3-diamine (8.70 g), cyanogen bromide (6.04 g), THF (80 ml) and water (20 ml) was stirred at room temperature for 24 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 washed with ethyl acetate, treated with activated carbon, and recrystallized from methanol to give the title compound (5.60 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. washThe residue was washed with ethyl acetate
  6. additiontreated with activated carbon
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-575689dd69734f7586fe74c67685dbd4
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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