m-Toluidine → HCID 118699715, compound

HRID 1773303Notes

Reaction equation

HRID 1773303 reaction equation
[CH2:1]1[CH2:10][N:9]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)[CH2:8][C:7]2[CH:6]=[N:5][C:4]3[CH:20]=[CH:21][CH:22]=[CH:23][C:3]=3[C:2]1=2.C(N(CC)CC)C.CCCP(=O)=O.[NH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH3:44])[CH:39]=1>CN(C=O)C>[CH2:1]1[CH2:10][N:9]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([CH3:44])[CH:39]=2)=[O:16])[CH2:8][C:7]2[CH:6]=[N:5][C:4]3[CH:20]=[CH:21][CH:22]=[CH:23][C:3]=3[C:2]1=2

Participants

6

Reactant 4

HCID 7934m-ToluidineHCID 8471TriethylamineHCID 16167369Propylphosphoric anhydrideHCID 118699718HCID 118699718, compound

Product 1

HCID 118699715HCID 118699715, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(1,4-dihydrobenzo[c]-2,7-naphthyridin-3(2H)-yl)benzoic acid (0.20 mmol, 61 mg) and triethylamine (0.40 mmol, 0.056 mL) in 1.6 mL DMF at rt was added propylphosphonic anhydride solution (50 wt % in EtOAc, 0.24 mmol, 0.143 mL). After 15 min at rt, meta-toluidine (0.30 mmol, 0.032 mL) was added and the reaction stirred at rt for 18 hours. The reaction was quenched into dilute aqueous Na2CO3 solution, extracted into EtOAc, the EtOAc layer washed with H2O, dilute aqueous Na2CO3 solution, brine, dried with anhydrous Na2SO4 and concentrated. The resulting solid was chromatographed eluting with CHCl3/EtOAc and then recrystallized from EtOAc/hexane to give the title compound as an off-white solid (38 mg, 48%).

Workup

  1. customThe reaction was quenched into dilute aqueous Na2CO3 solution
  2. extractionextracted into EtOAc
  3. washthe EtOAc layer washed with H2O, dilute aqueous Na2CO3 solution, brine
  4. dry with materialdried with anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe resulting solid was chromatographed
  7. washeluting with CHCl3/EtOAc
  8. customrecrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-7dbb0af0c2944e5380d3762ac99beac3
Source dataset
uspto-grants-2016_02
Patent number
US09255096B1

Reaction notes

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