Trifluoroacetic acid → HCID 86631144, compound

HRID 912720Notes

Reaction equation

HRID 912720 reaction equation
C(N=[C:10]=[S:11])(=O)C1C=CC=CC=1.[C:12]([C:15]1[NH:19][CH:18]=[N:17][C:16]=1[NH:20][CH2:21][CH2:22][NH:23]C(=O)OC(C)(C)C)(=[O:14])[NH2:13].[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34]>ClCCl.CO>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[NH2:23][CH2:22][CH2:21][N:20]1[C:16]2[N:17]=[CH:18][NH:19][C:15]=2[C:12](=[O:14])[NH:13][C:10]1=[S:11]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 68284Benzoyl isothiocyanateHCID 86631143tert-Butyl {2-[(5-carbamoyl-1H-imidazol-4-yl)amino]ethyl}carbamate

Product 1

HCID 86631144HCID 86631144, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
80 °C

Procedure

Benzoyl isothiocyanate (1.3 mL, 9.8 mmol) was added to tert-butyl {2-[(5-carbamoyl-1H-imidazol-4-yl)amino]ethyl}carbamate (2.5 g, 9.3 mmol, obtained from Example 26(a)) in dichloromethane (25 mL) and methanol (0.050 mL) at 0° C. The mixture was allowed to reach r.t. and stirred for 3 h. After removal of solvents, the residue was dissolved in ammonia (7 N in methanol, 30 mL) and subjected to microwave heating at 80° C. for 5 h. The solvent was then evaporated and the Boc-protected product was purified by silica gel column chromatography (dichloromethane/methanol 95:5) which gave 1.5 g (52% yield). This material (1.5 g, 4.9 mmol) was dissolved in dichloromethane (50 mL) and treated with trifluoroacetic acid (7 mL). After 2 h, the mixture was concentrated, diethyl ether was added and the solid was collected and dried in vacuo to afford 1.1 g (67% yield) of the title compound as its trifluoroacetic acid salt.

Workup

  1. customto reach r.t.
  2. customAfter removal of solvents
  3. dissolutionthe residue was dissolved in ammonia (7 N in methanol, 30 mL)
  4. customThe solvent was then evaporated
  5. customwas purified by silica gel column chromatography (dichloromethane/methanol 95:5) which
  6. customgave 1.5 g (52% yield)
  7. waitAfter 2 h
  8. concentrationthe mixture was concentrated
  9. additiondiethyl ether was added
  10. customthe solid was collected
  11. customdried in vacuo

Sources & evidence

ORD record
ord-6210b43854a04d468251d70fe31aa95f
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

Loading…