1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59813391, compound

HRID 1925318Notes

Reaction equation

HRID 1925318 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH:20]=[CH:21][C:22]([NH2:26])=[CH:23]2)=[CH:18][CH:17]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:48][C:49]1[CH:57]=[CH:56][C:52]([C:53](O)=[O:54])=[CH:51][C:50]=1[C:58]([F:61])([F:60])[F:59].CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH:20]=[CH:21][C:22]([NH:26][C:53](=[O:54])[C:52]3[CH:56]=[CH:57][C:49]([Cl:48])=[C:50]([C:58]([F:61])([F:59])[F:60])[CH:51]=3)=[CH:23]2)=[CH:18][CH:17]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27738574-Chloro-3-(trifluoromethyl)benzoic acidHCID 67520515HCID 67520515, compound

Product 1

HCID 59813391HCID 59813391, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(6,7-dimethoxyquinolin-4-yloxy)naphthalen-2-amine (0.137 g, 0.40 mmol) in 10 mL of DMF was added EDCI (0.077 g, 0.40 mmol), HOBt (0.054 g, 0.40 mmol), and 4-chloro-3-(trifluoromethyl)benzoic acid (0.099 g, 0.44 mmol). DIPEA (0.140 mL, 0.80 mmol) was added and the solution was stirred for 16 h at RT under an atmosphere of nitrogen. The reaction was diluted with water and extracted with EtOAc 3×. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a Gilson Prep HPLC system. The fractions were collected, combined, treated with NaHCO3(aq) and extracted with EtOAc 3×. The organic layer was dried (Na2SO4), filtered and concentrated to afford the desired compound. MS (ESI, pos. ion) m/z: 553.0 (M+1). Mass Calc'd for C29H20ClF3N2O4: 552.934.

Workup

  1. extractionextracted with EtOAc 3×
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customThe fractions were collected
  8. additiontreated with NaHCO3(aq)
  9. extractionextracted with EtOAc 3×
  10. dry with materialThe organic layer was dried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-908d249257ca4f9f99cc28e56dd27892
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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