Trifluoroacetic acid → HCID 86705336, compound

HRID 571129Notes

Reaction equation

HRID 571129 reaction equation
C([O:5][C:6]([C:8]1[S:9][C:10]([CH2:13][C:14]([CH3:20])([C:16]([O:18]C)=[O:17])[CH3:15])=[CH:11][CH:12]=1)=O)(C)(C)C.Cl.[F:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[OH:32])[C:26]([NH2:28])=[NH:27].CCN=C=NCCCN(C)C.Cl.[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48]>>[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].[C:26]([C:25]1[CH:29]=[CH:30][C:31]([O:32][C:6]([C:8]2[S:9][C:10]([CH2:13][C:14]([CH3:20])([CH3:15])[C:16]([OH:18])=[O:17])=[CH:11][CH:12]=2)=[O:5])=[C:23]([F:22])[CH:24]=1)(=[NH:28])[NH2:27]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86346253HCID 86346253, compoundHCID 135741553HCID 135741553, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.1%HCID 86705336HCID 86705336, compoundYield 35%

Procedure

To 5-(2-Methyl-2-methoxycarbonylpropyl)thiophene-2-carboxylic acid tert-butyl ester (5.0 g, 16.8 mmol) was added trifluoroacetic acid (20 mL), and the mixture was stirred at room temperature for 30 minutes. The solvent was evaporated, and the residue was dissolved in pyridine (30 mL), 3-fluoro-4-hydroxybenzamidine hydrochloride (3.2 g, 16.8 mmol) and WSC hydrochloride (3.8 g, 19.8 mmol) were added, and the mixture was stirred at 50° C. for 5 hours. The reaction mixture was concentrated under reduced pressure, 4N-hydrochloric acid solution (10 mL) and 4N-Hydrogen chloride in 1,4-Dioxane (10 mL) were added to the obtained residue, and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by high performance liquid chromatography (water-acetonitrile, each containing 0.1% trifluoroacetic acid) to give the title compound (2.8 g, 5.86 mmol, 35%).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in pyridine (30 mL)
  3. stirringthe mixture was stirred at 50° C. for 5 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure, 4N-hydrochloric acid solution (10 mL) and 4N-Hydrogen chloride in 1,4-Dioxane (10 mL)
  5. additionwere added to the obtained residue
  6. stirringthe mixture was stirred at 80° C. for 2 hours
  7. concentrationThe reaction mixture was concentrated under reduced pressure
  8. customthe obtained residue was purified by high performance liquid chromatography (water-acetonitrile

Sources & evidence

ORD record
ord-822489f64e074aa6b3f71772b4402163
Source dataset
uspto-grants-2015_05
Patent number
US09024044B2

Reaction notes

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