3-(Trifluoromethyl)aniline → HCID 118699731, compound

HRID 1773307Notes

Reaction equation

HRID 1773307 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.[F:37][C:38]([F:47])([F:46])[C:39]1[CH:40]=[C:41]([CH:43]=[CH:44][CH:45]=1)[NH2:42]>CN(C1C=CN=CC=1)C.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:42][C:41]2[CH:43]=[CH:44][CH:45]=[C:39]([C:38]([F:37])([F:46])[F:47])[CH:40]=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

7

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 8471TriethylamineHCID 16167369Propylphosphoric anhydrideHCID 118699718HCID 118699718, compound

Product 1

HCID 118699731HCID 118699731, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 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), triethylamine (0.40 mmol, 0.056 mL), and catalytic DMAP 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, 3-(trifluoromethyl)aniline (0.30 mmol, 0.037 mL) was added and the reaction stirred at rt for 24 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 a light yellow solid (59 mg, 66%).

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 and rotary evaporated
  5. customThe resulting solid was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-012dc6b44d28498eb986da88ce55316d
Source dataset
uspto-grants-2016_02
Patent number
US09255096B1

Reaction notes

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