3-Ethylaniline → HCID 118699724, compound

HRID 1773320Notes

Reaction equation

HRID 1773320 reaction equation
[S:1]1[C:13]2[C:12]3[CH2:11][CH2:10][N:9]([C:14]4[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=4)[C:17]([OH:19])=O)[CH2:8][C:7]=3[CH:6]=[N:5][C:4]=2[CH:3]=[CH:2]1.C(N(CC)C(C)C)(C)C.CCCP(=O)=O.[CH2:38]([C:40]1[CH:41]=[C:42]([CH:44]=[CH:45][CH:46]=1)[NH2:43])[CH3:39]>CN(C1C=CN=CC=1)C.ClCCCl>[S:1]1[C:13]2[C:12]3[CH2:11][CH2:10][N:9]([C:14]4[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=4)[C:17]([NH:43][C:42]4[CH:44]=[CH:45][CH:46]=[C:40]([CH2:38][CH3:39])[CH:41]=4)=[O:19])[CH2:8][C:7]=3[CH:6]=[N:5][C:4]=2[CH:3]=[CH:2]1

Participants

7

Reactant 4

HCID 114753-EthylanilineHCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 118699727HCID 118699727, compound

Product 1

HCID 118699724HCID 118699724, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 3-(8,9-dihydrothieno[3,2-c]-2,7-naphthyridin-7(6H)-yl)benzoic acid (0.113 mmol, 35 mg), N, N-diisopropylethylamine (0.339 mmol, 0.059 mL), and catalytic DMAP in 1.2 mL 1,2-dichloroethane at rt was added propylphosphonic anhydride solution (50 wt % in EtOAc, 0.136 mmol, 0.081 mL). After 7 min at rt, 3-ethylaniline (0.17 mmol, 0.021 mL) was added and the reaction stirred at rt for 5 hours. The reaction was quenched into dilute aqueous NaHCO3 solution, extracted with EtOAc, the EtOAc layer washed with H2O, dilute aqueous NaHCO3 solution, brine, dried with anhydrous Na2SO4 and rotary evaporated. The resulting oil was chromatographed eluting with EtOAc/CDCl3 to give the title compound as a light yellow solid (32 mg, 69%).

Workup

  1. customThe reaction was quenched into dilute aqueous NaHCO3 solution
  2. extractionextracted with EtOAc
  3. washthe EtOAc layer washed with H2O, dilute aqueous NaHCO3 solution, brine
  4. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  5. customThe resulting oil was chromatographed
  6. washeluting with EtOAc/CDCl3

Sources & evidence

ORD record
ord-9b69356f21f14141b1f8e9985e9f7905
Source dataset
uspto-grants-2016_02
Patent number
US09255096B1

Reaction notes

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