Trifluoroacetic acid → HCID 58486411, compound

HRID 1890764Notes

Reaction equation

HRID 1890764 reaction equation
FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[N:23]=[N:24][C:25]([C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)=[C:26]([CH3:29])[C:27]=2[CH3:28])[CH2:18][CH2:17]1)C)(C)(C)C>C(Cl)Cl>[CH3:28][C:27]1[C:26]([CH3:29])=[C:25]([C:30]2[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=2)[N:24]=[N:23][C:22]=1[N:19]1[CH2:18][CH2:17][CH:16]([NH:14][CH3:13])[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58486422HCID 58486422, compound

Product 1

HCID 58486411HCID 58486411, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add CH2Cl2 (20 mL) and trifluoroacetic acid (20 mL) to tert-butyl-1-(4,5-dimethyl-6-(pyridine-4-yl)pyridazin-3-yl)piperidin-4-yl(methyl)carbamate (1.19 g, 2.99 mmol). Stir at ambient temperature for 3 d. Concentrate under reduced pressure to give a residue. Partition the residue between CH2Cl2 and 1 N NaOH. Separate the layers, and extract the aqueous layer twice with CH2Cl2. Combine the organic extracts, dry over Na2SO4, filter, and concentrate under reduced pressure to obtain the title compound (790 mg, 89%). ES/MS m/z 298.2 (M+1).

Workup

  1. concentrationConcentrate under reduced pressure
  2. customto give a residue
  3. customPartition the residue between CH2Cl2 and 1 N NaOH
  4. customSeparate the layers
  5. extractionextract the aqueous layer twice with CH2Cl2
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-7571ac7d5648428e8e4067f185c018d2
Source dataset
uspto-grants-2013_08
Patent number
US08507490B2

Reaction notes

Loading…