Dimethylformamide → HCID 66962792, compound

HRID 1360664Notes

Reaction equation

HRID 1360664 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[C:8](NC)[C:9]([F:14])=[C:10](F)[CH:11]=2)[C:6](=[O:17])[C:5]([C:18]([O:20]CC)=O)=[CH:4]1)[CH3:2].[CH2:23]([O:25][C:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)=[O:27])[CH3:24].[CH3:34][CH2:35][N:36]=C=NCCCN(C)C.Cl.O[N:47]1[C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][C:50]=2N=N1.CN(C=[O:60])C>>[CH:51]1([NH:47][C:10]2[CH:11]=[C:12]3[C:7]([C:6](=[O:17])[C:5]([C:18]([NH:36][CH2:35][C:34]([N:31]4[CH2:30][CH2:29][N:28]([C:26]([O:25][CH2:23][CH3:24])=[O:27])[CH2:33][CH2:32]4)=[O:60])=[O:20])=[CH:4][N:3]3[CH2:1][CH3:2])=[CH:8][C:9]=2[F:14])[CH2:50][CH2:55][CH2:54][CH2:53][CH2:52]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23117811HCID 23117811, compound

Product 1

HCID 66962792HCID 66962792, compound

Procedure

210 mg of the compound of Example 161 was suspended in 5.0 ml of DMF, to which 0.1 ml of ethoxycarbonylpiperazine, 130 mg of WSC.HCl and 100 mg of 1-hydroxybenzotriazole were added sequentially to the resulting reaction mixture under ice cooling, for stirring at ambient temperature for 17 hours. The reaction mixture was concentrated under reduced pressure, to which water was added for chloroform extraction. The resulting organic layer was washed sequentially with aqueous saturated NaHCO3 and aqueous saturated sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure. The resulting solid was washed with EtOH, to obtain 228 mg of ethyl 4-[({[7-(cyclohexylamino)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]carbonyl}amino)acetyl]piperazine-1-carboxylate.

Workup

  1. additionwere added sequentially to the resulting reaction mixture under ice cooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure, to which water
  3. additionwas added for chloroform extraction
  4. washThe resulting organic layer was washed sequentially with aqueous saturated NaHCO3 and aqueous saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washThe resulting solid was washed with EtOH

Sources & evidence

ORD record
ord-75f92b551a844286b0c21869fd5ac69f
Source dataset
uspto-grants-2011_02
Patent number
US07879878B2

Reaction notes

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