Trifluoroacetic acid → HCID 22912861, compound

HRID 1736720Notes

Reaction equation

HRID 1736720 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 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-856540e26bd447d0998ad5d50bc12fb1
Source dataset
uspto-grants-1996_07
Patent number
US05541324

Reaction notes

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