Trifluoroacetic acid → HCID 10043381, compound

HRID 855555Notes

Reaction equation

HRID 855555 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH:7][C:8](/[C:10](/[C:17]2[CH:18]=[CH:19][C:20]([NH:23]C(=O)OC(C)(C)C)=[N:21][CH:22]=2)=[CH:11]/[CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:9])=[N:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CCOCC>[NH2:23][C:20]1[N:21]=[CH:22][C:17](/[C:10](=[CH:11]\[CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)/[C:8]([NH:7][C:5]2[S:6][C:2]([Cl:1])=[CH:3][N:4]=2)=[O:9])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58935727HCID 58935727, compound

Product 1

HCID 10043381HCID 10043381, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of (E)-tert-butyl {5-[1-(5-chlorothiazol-2-ylcarbamoyl)-2-cyclopentylvinyl]pyridin-2-yl}carbamate (Preparation 18, 212 mg, 473 μmol) in CH2Cl2 (5 mL) was treated with TFA (5 mL, 65.1 mmol). After 2 h, the mixture was evaporated to dryness, then EtOAc (60 mL) was added. The EtOAc solution was washed with H2O-saturated aqueous NaHCO3 (1:1, 20 mL) and brine (20 mL), before being dried (MgSO4). Filtration and solvent evaporation gave a residue that was dissolved in a minimal amount of Et2O. IH was added to the Et2O solution to precipitate a solid, which was collected and dried to furnish the title compound: RTA=3.07 min; m/z (ES+)=349.2 [M+H]+.

Workup

  1. customthe mixture was evaporated to dryness
  2. additionEtOAc (60 mL) was added
  3. washThe EtOAc solution was washed with H2O-saturated aqueous NaHCO3 (1:1, 20 mL) and brine (20 mL)
  4. dry with materialbefore being dried (MgSO4)
  5. filtrationFiltration and solvent evaporation
  6. customgave a residue that
  7. customto precipitate a solid, which
  8. customwas collected
  9. customdried

Sources & evidence

ORD record
ord-f563985c750348788a4a59f238fe48bd
Source dataset
uspto-grants-2007_08
Patent number
US07262196B2

Reaction notes

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