Triethylamine → 5-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid [4-(4-ethyl-piperazin-1-yl)-phenyl]-amide

HRID 2391904Notes

Reaction equation

HRID 2391904 reaction equation
CCCP(=O)=O.[Cl:7][C:8]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([O:16][CH3:17])=[C:10]([Cl:18])[C:9]=1[C:19]1[CH:28]=[CH:27][C:26]([C:29](O)=[O:30])=[C:25]2[C:20]=1[CH:21]=[CH:22][CH:23]=[N:24]2.[CH2:32]([N:34]1[CH2:39][CH2:38][N:37]([C:40]2[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=2)[CH2:36][CH2:35]1)[CH3:33].CCN(CC)CC>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O.O>[CH2:32]([N:34]1[CH2:35][CH2:36][N:37]([C:40]2[CH:46]=[CH:45][C:43]([NH:44][C:29]([C:26]3[CH:27]=[CH:28][C:19]([C:9]4[C:10]([Cl:18])=[C:11]([O:16][CH3:17])[CH:12]=[C:13]([O:14][CH3:15])[C:8]=4[Cl:7])=[C:20]4[C:25]=3[N:24]=[CH:23][CH:22]=[CH:21]4)=[O:30])=[CH:42][CH:41]=2)[CH2:38][CH2:39]1)[CH3:33]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 9367384-(4-Ethylpiperazin-1-yl)anilineHCID 16167369Propylphosphoric anhydrideHCID 592929115-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid

Product 1

HCID 592928475-(2,6-Dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid [4-(4-ethyl-piperazin-1-yl)-phenyl]-amide

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of propylphosphonic anhydride (50% in DMF, 0.41 mL, 0.70 mmol, 2 equiv), 5-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid (Step 159.1) (132 mg, 0.35 mmol), 4-(4-ethylpiperazin-1-yl)-aniline (Step 1.9) (79 mg, 0.39 mmol, 1.1 equiv), DMAP (3 mg), and Et3N (0.49 mL, 3.5 mmol, 10 equiv) in DMF (3 mL), was stirred for 16 h at rt, under an argon atmosphere. The reaction mixture was diluted with EtOAc and H2O. The aqueous layer was separated and extracted with EtOAc. The combined organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by trituration in EtOAc to afford the title compound as a yellow solid: ES-MS: 564.9/566.9 [M+H]+; tR=4.45 min (System 1).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with EtOAc
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by trituration in EtOAc

Sources & evidence

ORD record
ord-8577e36d794a4863805c3b67ba9f1e70
Source dataset
uspto-grants-2012_09
Patent number
US08273882B2

Reaction notes

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