Triethylamine → HCID 118699714, compound

HRID 1773305Notes

Reaction equation

HRID 1773305 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:41]=[C:42]([CH:44]=[CH:45][CH:46]=1)[NH2:43])([CH3:39])[CH3:38]>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:43][C:42]2[CH:44]=[CH:45][CH:46]=[C:40]([CH:37]([CH3:39])[CH3:38])[CH:41]=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 8471TriethylamineHCID 4586793-IsopropylanilineHCID 16167369Propylphosphoric anhydrideHCID 118699718HCID 118699718, compound

Product 1

HCID 118699714HCID 118699714, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(1,4-dihydrobenzo[c]-2,7-naphthyridin-3(2H)-yl)benzoic acid (0.10 mmol, 30 mg) and triethylamine (0.20 mmol, 0.028 mL) in 1.0 mL DMF at rt was added propylphosphonic anhydride solution (50 wt % in EtOAc, 0.12 mmol, 0.072 mL). After 15 min at rt, 3-isopropylaniline (0.15 mmol, 0.021 mL) was added and the reaction stirred at rt for 4 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 triturated with EtOAc/hexane to give the title compound as a light beige solid (22 mg, 52%).

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 triturated with EtOAc/hexane

Sources & evidence

ORD record
ord-a8368d23fe57413e8536d0bec75d28c8
Source dataset
uspto-grants-2016_02
Patent number
US09255096B1

Reaction notes

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