4-Isopropylaniline → HCID 118699728, compound

HRID 1773306Notes

Reaction equation

HRID 1773306 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](O)=[O:15])[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.[CH:37]([C:40]1[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=1)([CH3:39])[CH3:38]>ClCCCl>[CH2:1]1[CH2:10][N:9]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([NH:44][C:43]2[CH:45]=[CH:46][C:40]([CH:37]([CH3:39])[CH3:38])=[CH:41][CH:42]=2)=[O:15])[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 74644-Isopropylaniline2×HCID 8471TriethylamineHCID 16167369Propylphosphoric anhydrideHCID 118699718HCID 118699718, compound

Product 1

HCID 118699728HCID 118699728, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

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 2.0 mL 1,2-dichloroethane at rt was added propylphosphonic anhydride solution (50 wt % in EtOAc, 0.24 mmol, 0.143 mL). After 10 min at rt, 4-isopropylaniline (0.30 mmol, 0.043 mL) was added and the reaction stirred at rt for 1 hour. Then an additional 0.015 mL 4-isopropylaniline was added, the reaction heated at 60° C. for 5 min, then continued at rt for 3 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 rotary evaporated. The resulting solid was recrystallized from EtOAc/hexane to give the title compound as an off-white solid (52 mg, 62%).

Workup

  1. temperaturethe reaction heated at 60° C. for 5 min
  2. waitcontinued at rt for 3 hours
  3. customThe reaction was quenched into dilute aqueous Na2CO3 solution
  4. extractionextracted into EtOAc
  5. washthe EtOAc layer washed with H2O, dilute aqueous Na2CO3 solution, brine
  6. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  7. customThe resulting solid was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-86f5b7b9a7dd4dcd82074e82d121765b
Source dataset
uspto-grants-2016_02
Patent number
US09255096B1

Reaction notes

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