HCID 86673319, compound → HCID 74983044, compound

HRID 517339Notes

Reaction equation

HRID 517339 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:11]1[CH:29]=[CH:28][C:14]([O:15][C:16]([C:18]2[S:22][C:21]([CH2:23][CH2:24][C:25]([OH:27])=O)=[CH:20][CH:19]=2)=[O:17])=[C:13]([F:30])[CH:12]=1)(=[NH:10])[NH2:9]>S(Cl)(Cl)=O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:11]1[CH:29]=[CH:28][C:14]([O:15][C:16]([C:18]2[S:22][C:21]([CH2:23][CH2:24][C:25]([N:9]([CH2:8][CH:11]=[CH2:12])[CH2:2][C:3]([OH:5])=[O:4])=[O:27])=[CH:20][CH:19]=2)=[O:17])=[C:13]([F:30])[CH:12]=1)(=[NH:10])[NH2:9]

Participants

4

Reactant 1

HCID 86673319HCID 86673319, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.1%HCID 74983044HCID 74983044, compoundYield 167.9%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

3-[5-(4-Amidino-2-fluorophenoxycarbonyl)thiophen-2-yl]propanoic acid trifluoroacetic acid salt (38 mg, 0.084 mmol) was dissolved in thionyl chloride (500 μL), and the mixture was stirred at room temperature for 20 minutes. The reaction mixture was concentrated under reduced pressure, M-21 (18.8 mg, 0.11 mmol), dichloromethane (200 μL) and pyridine (300 μL) were added to the obtained residue, and the mixture was stirred for 90 minutes. The reaction mixture was concentrated under reduced pressure, trifluoroacetic acid (500 μL) was added to the obtained residue, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by high performance liquid chromatography (acetonitrile-water, each containing 0.1% trifluoroacetic acid, 5-35%) to give the title compound (25.5 mg, 0.047 mmol, 55%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, M-21 (18.8 mg, 0.11 mmol), dichloromethane (200 μL) and pyridine (300 μL)
  2. additionwere added to the obtained residue
  3. stirringthe mixture was stirred for 90 minutes
  4. concentrationThe reaction mixture was concentrated under reduced pressure, trifluoroacetic acid (500 μL)
  5. additionwas added to the obtained residue
  6. stirringthe mixture was stirred at room temperature for 30 minutes
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. customthe obtained residue was purified by high performance liquid chromatography (acetonitrile-water

Sources & evidence

ORD record
ord-5202064a9abb470dafcb26a8d7b325ff
Source dataset
uspto-grants-2015_08
Patent number
US09115107B2

Reaction notes

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