Acetic Acid → HCID 118159764, compound

HRID 628285Notes

Reaction equation

HRID 628285 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[CH:4][CH:3]=1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:10]([NH:9][C:5]1[C:6]([NH2:8])=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 106306156-Chloropyridine-2,3-diamine

Product 1

HCID 118159764HCID 118159764, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 6-chloro-2,3-diaminopyridine (2.00 g, 13.9 mmol, Combi-Blocks) and benzaldehyde (1.48 g, 13.9 mmol, Aldrich) in 1,2-dichloroethane (50 mL) was treated with acetic acid (0.2 mL, 3 mmol) and the mixture was allowed to stir for 30 minutes. Na(OAc)3BH (8.8 g, 42 mmol) was added and the reaction was stirred overnight. The reaction was quenched with water, then poured into saturated NaHCO3 solution. The product was extracted with three portions of DCM, and the combined extracts were washed with saturated NaHCO3 solution and brine, dried over sodium sulfate, filtered and concentrated. Flash chromatography, eluting with a gradient from 0-75% EtOAc in hexanes was used to afford purified product.

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe reaction was quenched with water
  3. additionpoured into saturated NaHCO3 solution
  4. extractionThe product was extracted with three portions of DCM
  5. washthe combined extracts were washed with saturated NaHCO3 solution and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washFlash chromatography, eluting with a gradient from 0-75% EtOAc in hexanes
  10. customto afford
  11. custompurified product

Sources & evidence

ORD record
ord-fd272dada59941b7a6d350a1e4edb1af
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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