Trifluoroacetic acid → HCID 70143916, compound

HRID 611795Notes

Reaction equation

HRID 611795 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[C:10](=[O:21])[CH:9]1[CH:22]([C:24]1[N:28]([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=2)[CH:27]=[N:26][CH:25]=1)[OH:23])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[ClH:20].[Cl:20][C:16]1[CH:15]=[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH:9]([CH:22]([C:24]3[N:28]([CH2:29][C:30]4[CH:31]=[CH:32][C:33]([C:36]#[N:37])=[CH:34][CH:35]=4)[CH:27]=[N:26][CH:25]=3)[OH:23])[C:10]2=[O:21])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67612488HCID 67612488, compound

Product 1

HCID 70143916HCID 70143916, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the piperazinone from Step J (60 mg, 0.115 mmol) in 2 mL of dichloromethane at 0 ° C. was added trifluoroacetic acid (1.0 mL), and the reaction was allowed to warm to room temperature. After 6 hours, the solution was concentrated in vacuo, taken up in CH2Cl2, washed with dilute aq. NaHCO3 soln., dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. After conversion to the HCl salt, the product was isolated (62 mg) as a 9:1 mixture of diastereomers. FAB ms: 422 (M+1). Anal. Calc for C22H20ClN5O2.2.10 HCl. 1.00 H2O: C, 51.16; H, 4.70; 0, 13.56. Found: C, 51.21; H, 4.70; 0, 12.66.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. washwashed with dilute aq. NaHCO3 soln
  3. dry with material, dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide the crude product

Sources & evidence

ORD record
ord-75d15a1c14c943cbb992a16c81299c3f
Source dataset
uspto-grants-1999_12
Patent number
US06001835

Reaction notes

Loading…