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Pyridine → HCID 76607225, compound

HRID 2099320
Notes
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Reaction equation

HRID 2099320 reaction equation
[Cl:1][C:2]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:3]=1[CH2:4][NH:5][C:6]([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[C:12]([O:28][CH3:29])[C:13]([N:20]3[CH2:25][CH:24]([CH3:26])[NH:23][CH:22]([CH3:27])[CH2:21]3)=[C:14]([F:19])[CH:15]=2)[N:10]([CH2:30][C:31]([F:34])([F:33])[F:32])[CH:9]=1)=[O:7].N1C=CC=CC=1.[Cl-].[C:47]([O:52][CH2:53][CH3:54])(=[O:51])[C:48]([O-])=[O:49]>ClCCl.C(OCC)(=O)C>[CH2:53]([O:52][C:47](=[O:51])[C:48]([N:23]1[CH:22]([CH3:27])[CH2:21][N:20]([C:13]2[C:12]([O:28][CH3:29])=[C:11]3[C:16]([C:17](=[O:18])[C:8]([C:6]([NH:5][CH2:4][C:3]4[CH:35]=[CH:36][C:37]([Cl:39])=[CH:38][C:2]=4[Cl:1])=[O:7])=[CH:9][N:10]3[CH2:30][C:31]([F:33])([F:34])[F:32])=[CH:15][C:14]=2[F:19])[CH2:25][CH:24]1[CH3:26])=[O:49])[CH3:54]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1049PyridineHCID 22632797Monoethyl oxalate monochlorideHCID 76607220N-(2,4-Dichlorobenzyl)-7-[(3RS,5RS)-3,5-dimethylpiperazin-1-yl]-6-fluoro-8-methoxy-1-(2,2,2-trifluoroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

Product 1

HCID 76607225HCID 76607225, compound

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

200 mg of the compound from Example 37A are dissolved in 3 ml of dichloromethane and 0.26 ml of pyridine and 71 μl of ethyl oxalate chloride are then added. The mixture is stirred at RT for 3 h. For the work-up, the mixture is diluted with ethyl acetate, and extracted by shaking twice with water, once with a saturated sodium hydrogen carbonate solution and once with a saturated sodium chloride solution. The organic phase is dried over sodium sulfate, concentrated in vacuo, and dried under high vacuum. 220 mg of the title compound are obtained.

Workup

  1. extractionextracted
  2. stirringby shaking twice with water, once with a saturated sodium hydrogen carbonate solution and once with a saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-77f406cd9c014c2498fa7c3a739e33ee
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07569563B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes