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Sodium Acetate → HCID 10117620, compound

HRID 1791123
Notes
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Reaction equation

HRID 1791123 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[C:10]([C:15](=O)[CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][S:20][CH2:19]1)[C:11]([O:13][CH3:14])=[O:12].Cl.[F:25][C:26]1[C:27]([C:33](=[NH:35])[NH2:34])=[N:28][CH:29]=[C:30]([F:32])[CH:31]=1.C([O-])(=O)C.[Na+]>C(O)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:15]([CH2:16][CH2:17][N:18]2[CH2:22][CH2:21][S:20][CH2:19]2)[NH:35][C:33]([C:27]2[C:26]([F:25])=[CH:31][C:30]([F:32])=[CH:29][N:28]=2)=[N:34]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 220278403,5-Difluoropyridine-2-carboximidamide--hydrogen chloride (1/1)HCID 69588140HCID 69588140, compound

Product 1

HCID 10117620HCID 10117620, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 0.20 g (0.56 mmol) of the compound from Example IX in 5 ml of isopropanol is heated together with 0.11 g (0.56 mmol) of the compound from Example VI and 0.06 g (0.67 mmol) of sodium acetate under reflux for 2 hours. The reaction mixture is concentrated, and the residue is taken up in ethyl acetate and extracted with dilute hydrochloric acid. The aqueous phase is made alkaline with dilute sodium hydroxide solution and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated. The residue is chromatographed on silica gel with cyclohexane/ethyl acetate (5:1→3:1) as mobile phase.

Workup

  1. temperatureunder reflux for 2 hours
  2. concentrationThe reaction mixture is concentrated
  3. extractionextracted with dilute hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel with cyclohexane/ethyl acetate (5:1→3:1) as mobile phase

Sources & evidence

ORD record
ord-2fba051fc5664ebf804df2ddb251efca
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07074784B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes