Trifluoroacetic acid → HCID 70872913, compound

HRID 1959323Notes

Reaction equation

HRID 1959323 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[C:24]([N:26]([CH2:33][CH3:34])[CH:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[C:23]([CH3:35])=[C:22]([C:36](=[O:48])[NH:37][CH2:38][C:39]4[C:40](=[O:47])[NH:41][C:42]([CH3:46])=[CH:43][C:44]=4[CH3:45])[CH:21]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:15]=[CH:16][C:17]([C:20]3[CH:25]=[C:24]([N:26]([CH2:33][CH3:34])[CH:27]4[CH2:28][CH2:29][O:30][CH2:31][CH2:32]4)[C:23]([CH3:35])=[C:22]([CH:21]=3)[C:36]([NH:37][CH2:38][C:39]3[C:40](=[O:47])[NH:41][C:42]([CH3:46])=[CH:43][C:44]=3[CH3:45])=[O:48])=[CH:18][CH:19]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86672673HCID 86672673, compound

Product 1

HCID 70872913HCID 70872913, compoundYield 903.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl(1-(5-(3-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl) carbamoyl)-5-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-4-methylphenyl)pyridin-2-yl)piperidin-4-yl)carbamate (0.39 g, 0.058 mmol) in DCM (4 mL) at 0° C., TFA (2 mL) was added and reaction was stirred for 1 h at room temperature. After completion, reaction was concentrated to dryness. The residue was then basified with aqueous sat. bicarbonate solution (30 mL) till pH 8 and aqueous layer extracted with 20% methanol in DCM (50 mL×4). Combined organic phase was dried over Na2SO4 and solvent removed under reduced pressure to afford the title compound (0.3 g, 90.63%) which was used as such for next reaction.

Workup

  1. customreaction
  2. customAfter completion, reaction
  3. concentrationwas concentrated to dryness
  4. extractionextracted with 20% methanol in DCM (50 mL×4)
  5. dry with materialCombined organic phase was dried over Na2SO4 and solvent
  6. customremoved under reduced pressure

Sources & evidence

ORD record
ord-43d12cceffda40098fe694c7deaa92b2
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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