p-Toluenesulfonic acid → HCID 118159821, compound

HRID 628286Notes

Reaction equation

HRID 628286 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]([NH2:16])=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17](OCC)(OCC)(OCC)[CH3:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>CCO>[CH2:1]([N:8]1[C:9]2[C:10](=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[N:16]=[C:17]1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 66221Triethyl orthoacetateHCID 118159764HCID 118159764, compound

Product 1

HCID 118159821HCID 118159821, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N3-benzyl-6-chloropyridine-2,3-diamine (2.56 g, 11.0 mmol, from Step 1), triethyl orthoacetate (15.7 mL, 85.6 mmol, Aldrich) and p-toluenesulfonic acid (0.59 g, 3.4 mmol, Aldrich) in EtOH (55 mL) was heated to reflux for 1.5 hours. The reaction was cooled to room temperature and solvent was evaporated. The residue was partitioned between EtOAc and water. The organic layer was washed with saturated NaHCO3 solution, and brine, dried over sodium sulfate, filtered and concentrated. The product began to crystallize and was triturated with hexanes over the weekend. The white solid was isolated by filtration (2.0 g, 71%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. customsolvent was evaporated
  4. customThe residue was partitioned between EtOAc and water
  5. washThe organic layer was washed with saturated NaHCO3 solution, and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto crystallize
  10. customwas triturated with hexanes over the weekend
  11. customThe white solid was isolated by filtration (2.0 g, 71%)

Sources & evidence

ORD record
ord-ad3ed5d0c9b34bdb86cdafb3e4cd52a6
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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