Trifluoroacetic acid → HCID 67378126, compound

HRID 710583Notes

Reaction equation

HRID 710583 reaction equation
C(OC([N:8]([C:16]1[C:21]([F:22])=[C:20]([C:23]2[C:24](=[O:37])[N:25]([CH3:36])[C:26]3[C:31]([CH:32]=2)=[CH:30][N:29]=[C:28]([NH:33][CH2:34][CH3:35])[CH:27]=3)[C:19]([F:38])=[CH:18][N:17]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C:16]1[C:21]([F:22])=[C:20]([C:23]2[C:24](=[O:37])[N:25]([CH3:36])[C:26]3[C:31]([CH:32]=2)=[CH:30][N:29]=[C:28]([NH:33][CH2:34][CH3:35])[CH:27]=3)[C:19]([F:38])=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67378027HCID 67378027, compound

Product 1

HCID 67378126HCID 67378126, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-(N,N-bis-(t-butoxycarbonyl)amino)-3,5-difluoropyridin-4-yl)-7-(ethylamino)-1-methyl-1,6-naphthyridin-2(1H)-one (32 mg) in DCM (10 mL) was added trifluoroacetic acid (5 mL). The mixture was stirred at room temperature for 1 h. The solvent was removed and the residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic phase was washed with brine and was then dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed on silica gel (3% methanol in dichloromethane eluant) to provide the title compound. MS (m/z) 332.1 (M+1).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  3. washThe organic phase was washed with brine
  4. dry with materialwas then dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (3% methanol in dichloromethane eluant)

Sources & evidence

ORD record
ord-1ca1ab9c1c1d41a9bf69351b45dc4a1e
Source dataset
uspto-grants-2015_11
Patent number
US09181238B2

Reaction notes

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