Trifluoroacetic acid → HCID 22912861, compound

HRID 1378777Notes

Reaction equation

HRID 1378777 reaction equation
[N:1]1([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]3[CH:18]=[N:19][C:20]([C:21]([O:23]C(C)(C)C)=[O:22])=[C:10]3[CH2:9]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.ClCCl>C(OCC)(=O)C.CCCCCC>[N:1]1([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]3[CH:18]=[N:19][C:20]([C:21]([OH:23])=[O:22])=[C:10]3[CH2:9]2)=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21863450Trifluoroacetic acid methylene chloride2×HCID 22912827Tert-butyl 4,5-dihydro-5-[(pyrrolidino)carbonyl]imidazo[1,5-a]quinoxaline-3-carboxylate

Product 1

HCID 22912861HCID 22912861, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

To tert-butyl 4,5-dihydro-5-[(pyrrolidino)carbonyl]imidazo[1,5-a]quinoxaline-3 -carboxylate (I, EXAMPLE 217, 2.97 g) are added 20 ml of a solution of trifluoroacetic acid and dichloromethane (1/1). After stirring for 3.5 hr an additional 2 ml of the trifluoroacetic acid/dichloromethane solution are added, followed an hour later by another 2 ml and 30 min later with a final 2 ml of the trifluoroacetic acid/dichloromethane solution- The reaction is stirred 2 additional hours and then concentrated under reduced pressure. Dichloromethane is added to the residue and the mixture is again concentrated to give the title compound, which is crystallized from methanol/dichloromethane, mp 197°-200°; MS (m/z) at 312; NMR (DMSO-d6) 1.72, 3.15, 4.86, 7.18-7.22, 7.33, 7.90, 8.70 δ.

Workup

  1. additionare added
  2. concentrationconcentrated under reduced pressure
  3. additionDichloromethane is added to the residue
  4. concentrationthe mixture is again concentrated

Sources & evidence

ORD record
ord-f1c57966fac4488e90c26f96d9bfc329
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

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